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[ CAS No. 135484-83-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Chemical Structure| 135484-83-2

Chemical Structure| 135484-83-2

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Quality Control of [ 135484-83-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 135484-83-2 ]

CAS No. :	135484-83-2	MDL No. :	MFCD07783014
Formula :	C₈H₈BrNO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	MMSODGJNFCCKAZ-UHFFFAOYSA-N
M.W :	230.06	Pubchem ID :	17871390
Synonyms :

Calculated chemistry of [ 135484-83-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	49.83
TPSA :	52.32 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.05
Log Po/w (XLOGP3) :	3.36
Log Po/w (WLOGP) :	1.83
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	1.65
Consensus Log Po/w :	2.19

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.62
Solubility :	0.055 mg/ml ; 0.000239 mol/l
Class :	Soluble
Log S (Ali) :	-4.14
Solubility :	0.0168 mg/ml ; 0.000073 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.97
Solubility :	0.244 mg/ml ; 0.00106 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.46

Safety of [ 135484-83-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 135484-83-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 135484-83-2 ]
Downstream synthetic route of [ 135484-83-2 ]

[ 135484-83-2 ] Synthesis Path-Upstream 1~1

1
[ 135484-83-2 ]
[ 98-80-6 ]
[ 4445-43-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 13, p. 1595 - 1600

[ 135484-83-2 ] Synthesis Path-Downstream 1~8

1
[ 135484-83-2 ]
[ 62473-92-1 ]

Yield	Reaction Conditions	Operation in experiment
10%		Preparation 49 6-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one A solution of methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) in 20percent hydrochloric acid (30 mL) was stirred until all solids were dissolved. The solution was cooled to 0° C. and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise at such a rate that the internal reaction temperature did not exceed 5° C. The mixture was stirred at 0° C. for 45 minutes. Sulfur dioxide was bubbled into a mixture of acetic acid (50 mL) and water (5 mL) at 0° C. until the solution was saturated. Copper (I) chloride (2.0 g, 0.020 mol) was then added to the saturated sulfur dioxide solution. The mixture was cooled to 0° C. To this mixture was added the diazonium salt solution dropwise with vigorous stirring over a period of 30 minutes. The reaction mixture was stirred at 0° C. for 1 hour and then the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 2 h before it was poured into ice water (250 mL) and extracted with EtOAc (3*50 mL). The organics were washed with sat. NaHCO3 solution and dried over anhydrous Na2SO4. The solvent was removed in vacuo to afford an oily residue which was dissolved in tetrahydrofuran (40 mL) and cooled to 0° C. To this mixture was added a cold (0° C.) solution of ammonium hydroxide (28percent, 40 mL) portion-wise at such a rate that the internal reaction temperature was maintained below 10° C. The mixture was allowed to warm to room temperature and was then stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (40 mL) and washed with diethyl ether (50 mL). The aqueous layer was acidified with concentrated hydrochloric acid to pH 1. The resulting precipitate was collected by filtration and was dried under vacuum to produce of 6-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one (500 mg, 10percent yield). 1H NMR (400 MHz, DMSO) delta 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1, 1.5, 1H), 7.81 (d, J=8.0, 1H).
10%		solution of methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) in 20percent hydrochloric acid (30 mL) was stirred until all solids were dissolved. The solution was cooled to 0° C. and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise at such a rate that the internal reaction temperature did not exceed 5° C. The mixture was stirred at 0° C. for 45 minutes. Sulfur dioxide was bubbled into a mixture of acetic acid (50 mL) and water (5 mL) at 0° C. until the solution was saturated. Copper (I) chloride (2.0 g, 0.020 mol) was then added to the saturated sulfur dioxide solution. The mixture was cooled to 0° C. To this mixture was added the diazonium salt solution dropwise with vigorous stirring over a period of 30 minutes. The reaction mixture was stirred at 0° C. for 1 hour and then the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 2 h before it was poured into ice water (250 mL) and extracted with EtOAc (3*50 mL). The organics were washed with sat. NaHCO3 solution and dried over anhydrous Na2SO4. The solvent was removed in vacuo to afford an oily residue which was dissolved in tetrahydrofuran (40 mL) and cooled to 0° C. To this mixture was added a cold (0° C.) solution of ammonium hydroxide (28percent, 40 mL) portion-wise at such a rate that the internal reaction temperature was maintained below 10° C. The mixture was allowed to warm to room temperature and was then stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (40 mL) and washed with diethyl ether (50 mL). The aqueous layer was acidified with concentrated hydrochloric acid to pH 1. The resulting precipitate was collected by filtration and was dried under vacuum to produce of 6-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one (500 mg, 10percent yield). 1H NMR (400 MHz, DMSO) delta 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1, 1.5, 1H), 7.81 (d, J=8.0, 1H).

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 949 - 961
[2]Patent: US2008/9524,2008,A1 .Location in patent: Page/Page column 410
[3]Patent: US2015/231142,2015,A1 .Location in patent: Paragraph 1267

2
[ 158580-57-5 ]
[ 135484-83-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tin(II) chloride dihdyrate; In ethyl acetate; at 30℃; for 2h;Ultrasonic irradiation;	Example 281 : 2-(3-Chlorobenzo[b1thiophene-2-carboxarnido)-4-(5-(4-chlorophenyl)-2- oxo-oxazolidin-3-yl)benzoic acidMethod 36SnCI2 x 2H20 (5 g, 22 mmol) was added to a solution of <strong>[158580-57-5]methyl 4-bromo-2-nitrobenzoate</strong> (0.6 g, 2.3 mmol) in ethyl acetate (20 ml). The reaction mixture was submitted to ultrasonic irradiation for 2 h at 30C until the reaction was complete as indicated by TLC analysis. The solvent was removed under reduced pressure and the crude residue was washed with 2 M KOH. The aqueous layer was extracted with further portions of ethyl acetate, and the combined organic extracts were washed with brine and water, dried (MgS04) and concentrated under reduced pressure. The crude residue waschromatographed over silica gel (ethyl acetate / hexanes) yielding methyl 4-bromo-2- aminobenzoate (96%).A solution of this compound (0.46 g, 2 mmol), 5-(4-chlorophenyl)oxazolidin-2-one (0.4 g, 2 mmol), Xantphos (128 mg, 0.22 mmol), Pd2(dba)3 (92 mg, 0.11 mmol) and K3P04 (2.2 mmol) in dioxane was refluxed for 7 h. After cooling, the solvent was evaporated under vacuum and the residue partitioned between water and ethyl acetate. The aqueous layer was extracted with further portions of ethyl acetate and the combined organic extracts were washed with brine and water, dried (MgS04) and concentrated under reduced pressure. The crude residue was chromatographed over silica gel (ethyl acetate / hexanes) yielding methyl 2-amino-4-(5-(4-chlorophenyl)-2-oxo-oxazolidin-3-yl)benzoate (71 %).This compound (0.35 g, 1 mmol) was dissolved in THF, and 1.1 mmol of 3-chloro- benzo[b]thiophene carbonyl chloride was added. The reaction mixture was refluxed for 14 h and concentrated under vacuum. The crude reaction mass was washed with diethyl ether two times and dissolved in THF-water (3: 1). LiOH (1.1 mmol) was added and the solution was stirred overnight at room temperature, concentrated under vacuum, and the residue was dissolved in the minimum volume of water. After adjusting the pH to 6-7, the aqueous solution was extracted with ethyl acetate. The organic layer was dried (MgS04) and concentrated under vacuum to afford the title compound (50%), mp >200C.1 H NMR (400 MHz, DMSO-cfe) delta ppm: 13.70 (br.s, 1 H), 12.40 (br.s, 1 H), 8.93 (s, 1 H), 8.18 (m, 1 H), 8.09 (d, 1 H), 7.98 (m, 1 H), 7.64 (m, 2H), 7.59 (m, 2H), 7.53 (m, 3H), 5.83 (m, 1 H), 4.57 (m, 1 H), 4.04 (m, 1 H); MS: m/z = 527 [MH]+
96%	With hydrogen;5%-palladium/activated carbon; In methanol; under 2585.81 Torr; for 1h;	4-Bromo-2-aminomethylbenzoate : [00190] 4-Bromo-2-nitromethylbenzoate (300MG ; 1. 15MMOL) was dissolved in 25ML of methanol and shaken with 5% Pd (c) under hydrogen atmosphere (50 PSI) for 1 hour. The reaction was filtered through celite and evaporated to give the product as a white solid (255mg; 96%). MS: MH+= 230
93%	With tin(ll) chloride; In dichloromethane; ethyl acetate; at 20℃;	A. Methyl 2-amino-4-bromobenzoate To a stirred solution of 4-bromo-2-nitrobenzoic acid (EXAMPLE 5) (3.81 g, 15 mmol) in DMF (30 mL) at 0 C. was added 1,8-diazabicycloundecane (DBU) (10.3 mL, 75 mmol) followed by methyl iodide (4.67 mL, 75 mmol). The reaction mixture was stirred 15 min at 0 C. then allowed to warm to room temperature and stir overnight. The mixture was poured into water and extracted with EtOAc (2). The combined organic extracts were washed with water (2), dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexanes/EtOAc) to afford <strong>[158580-57-5]methyl 4-bromo-2-nitrobenzoate</strong> as a pale yellow solid (3.52 g, 90%).

93%		To a stirred solution of 4-bromo-2-nitrobenzoic acid (3.8 g, 15 mmol) in DMF (30 mL) at 0 C. was added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (10.0 mL, 75.0 mmol) followed by iodomethane (4.7 mL, 75 mmol). The reaction mixture was stirred 15 min at 0 C., then was allowed to warm to room temperature and was stirred overnight. The mixture was poured into H2O and extracted with EtOAc (2×). The combined organic extracts were washed with H2O (2×), dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexanes/EtOAc) to afford <strong>[158580-57-5]methyl 4-bromo-2-nitrobenzoate</strong> as a pale yellow solid (3.52 g, 0.90%). To a solution of the nitrobenzoate (3.52 g, 13.5 mmol) in 1:1 EtOAc/DCM (30 mL) at room temperature was added SnCl2.2H2O (15 g, 67 mmol). The reaction mixture was allowed to stir overnight. The solvents were evaporated in vacuo, and the residue was partitioned between satd. aq. NaHCO3 and DCM. The layers were separated, and the aqueous layer was further extracted with DCM (2×). The combined organic layers were dried (MgSO4) and concentrated in vacuo to provide the pure aminobenzoate as a white solid (2.89 g, 93%). 1H NMR (400 MHz, CDCl3): 7.70 (d, J=8.6 Hz, 1H), 6.84 (d, J=1.9 Hz, 1H), 6.75 (dd, J=8.6, 1.9 Hz, 1H), 5.78 (br s, 2H), 3.86 (s, 3H).
93%	With tin(ll) chloride; In dichloromethane; ethyl acetate; at 20℃; for 18h;Product distribution / selectivity;	B. Methyl 2-amino-4-bromobenzoate.; To a stirred solution of 4-bromo-2-nitrobenzoic acid (3.81 g, 15 mmol) in DMF (30 mL) at 0 C. was added 1,8-diazabicycloundecane (DBU; 10.3 mL, 75 mmol) followed by Mel (4.67 mL, 75 mmol). The mixture was stirred for 15 min at 0 C., then was allowed to warm to rt and was stirred overnight. The mixture was poured into water and extracted with EtOAc (2×). The combined organic extracts were washed with water (2×), dried (MgSO4), and concentrated. The residue was purified by flash chromatography (hexanes/EtOAc) to afford <strong>[158580-57-5]methyl 4-bromo-2-nitrobenzoate</strong> as a pale yellow solid (3.52 g, 90%). To a solution of the nitrobenzoate (3.52 g, 13.5 mmol) in 1:1 EtOAc/DCM (30 mL) at rt was added SnCl2.2H2O (15.27 g, 67 mmol). After 18 h, the mixture was concentrated, diluted with satd. aq. NaHCO3, and extracted with DCM (3×). The combined organic layers were dried (MgSO4) and concentrated to provide the desired aminobenzoate as a white solid (2.89 g, 93%). 1H NMR (400 MHz, CDCl3): 7.70(d, J=8.6, 1H), 6.84 (d, J=1.9, 1H), 6.75 (dd, J=8.6, 1.9, 1H), 5.78 (br s, 2H), 3.86 (s, 3H).
85%	With iron; acetic acid; at 20℃; for 2h;	To a solution of 1A (1.0 g, 3.85 mmol) in Acetic Acid (5 mL) was added iron powder (0.430 g, 7.69 mmol) and allowed to stir for 2 h at room temperature. Then reaction mixture was basified using 10% sodium carbonate (30 mL) and extracted with ethyl acetate (2*200 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude sample was purified by flash chromatography (5% Ethyl acetate: Pet ether; 12 g silica gel column) to afford 1B (off white solid 0.75 g, 3.26 mmol, 85% yield). LC-MS Anal. Calc'd for C8H8BrNO2 228.9, found [M+H] 230.3, Tr=0.98 min (Method DM)
84%		Step 2. Preparation of Methyl 2-amino-4-bromobenzoate Add tin (II) chloride (65.9 g, 292 mmol) to a suspension of methyl 4-bromo-2- nitrobenzoate (15.2 g, 58.4 mmol) in concentrated hydrochloric acid (120 mL) at room temperature and stir for 24 h. Slowly pour the mixture into water (700 mL) and adjust the pH to 9 with solid potassium hydroxide. Filter the white suspension through Celite, then stir the filter cake with ethyl acetate and filter that suspension. Separate the filtrate and extract the aqueous layer with ethyl acetate (200 mL). Combine the organic layers, dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford the title compound as an off-white solid (11.3 g, 84 %)
		Iron powder 2.6g was added to a mixed solution of methanol 20mL and acetic acid 20mL of <strong>[158580-57-5]methyl 4-bromo-2-nitrobenzoate</strong> 4.0g, it was heated and refluxed for 3 hours. After the reaction mixture was cooled to room temperature, saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added to it, and insoluble matter was filtrated. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, and solvent was removed under reduced pressure. Hexane was added to the obtained residue, solid matter was filtrated to give methyl 2-amino-4-bromobenzoate 2.0g of white solid. 1H-NMR(CDCl3) delta value: 3.89(3H,s),4.20(2H,s),7.26(1H,dd,J=8.3,2.1Hz),7.43(1H,d ,J=2.1Hz),7.47(1H,d,J=8.3Hz).

Reference： [1]Patent: WO2012/59442,2012,A2 .Location in patent: Page/Page column 111
[2]Patent: WO2005/32493,2005,A2 .Location in patent: Page/Page column 51
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 6371 - 6390
[4]Patent: US2004/224983,2004,A1 .Location in patent: Page 15
[5]Patent: US2005/38032,2005,A1 .Location in patent: Page/Page column 11
[6]Patent: US2006/69286,2006,A1 .Location in patent: Page/Page column 29; 61
[7]Patent: US2020/69695,2020,A1 .Location in patent: Paragraph 0292
[8]Patent: WO2005/37796,2005,A1 .Location in patent: Page/Page column 51
[9]Patent: WO2006/62093,2006,A1 .Location in patent: Page/Page column 56-57
[10]Patent: EP1860098,2007,A1 .Location in patent: Page/Page column 41

3
[ 7439-89-6 ]
[ 158580-57-5 ]
[ 135484-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bicarbonate; acetic acid; In methanol; hexane; ethyl acetate;	Referential Example 3 2.6 g of iron powder was added to a mixed solution of 20 mL of methanol and 20 mL of acetic acid containing 4.0 g of <strong>[158580-57-5]methyl 4-bromo-2-nitrobenzoate</strong>, and the resulting mixture was heated to reflux for 3 hours. After the reaction mixture was cooled to room temperature, a saturated sodium hydrogen carbonate aqueous solution and ethyl acetate were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. Hexane was added to the obtained residue and a solid substance was separated by filtration to obtain 2.0 g of methyl 2-amino-4-bromobenzoate as white solid. 1H-NMR (CDCl3) delta: 3.89 (3H, s), 4.20 (2H, s), 7.26 (1H, dd, J = 8.3, 2.1 Hz), 7.43 (1H, d, J = 2.1 Hz), 7.47 (1H, d, J = 8.3 Hz).

Reference： [1]Patent: EP1820795,2007,A1

4
[ 2882-15-7 ]
[ 135484-83-2 ]
[ 438535-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; cyclohexane;	5-Methoxy-2-methyl-3-indole acetic acid (5 g, obtainable from Acros), carbonyidiimidazole (4.44 g) and tetrahydrofuran (120 ml) were stirred at room temperature for 30 min after which methyl 4-bromoanthranilate (5.24 g) and pyridinium tosylate (13.69 g) were added and the mixture refluxed for 14 h. After diluting with dichloromethane (200 ml), the residue was washed with 2M hydrochloric acid (200 ml), 2M sodium hydroxide (200 ml), water (200 ml) and brine (200 ml) and dried (MgSO4). After solidifying by treatment with cyclohexane and ethyl acetate, the solid was triturated with ether to afford methyl 4-bromo-2-[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}benzoate (6.54 g), MH+ 433, 435; MH- 431, 433; TR 3.67 min.

Reference： [1]Patent: US2004/92569,2004,A1

5
copper (I) chloride [ No CAS ]
[ 135484-83-2 ]
[ 62473-92-1 ]

Yield	Reaction Conditions	Operation in experiment
10%	With ammonium hydroxide; acetic acid; sodium nitrite; In tetrahydrofuran; hydrogenchloride; water; sodium hydrogencarbonate;	Preparation 496-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-oneA solution of methyl 2-amino-4-bromobenzoate (4.5 g, 20 mmol) in 20percent hydrochloric acid (30 mL) was stirred until all solids were dissolved.The solution was cooled to 0° C. and a solution of sodium nitrite (1.4 g, 0.020 mol) in water (20 mL) was added dropwise at such a rate that the internal reaction temperature did not exceed 5° C.The mixture was stirred at 0° C. for 45 minutes.Sulfur dioxide was bubbled into a mixture of acetic acid (50 mL) and water (5 mL) at 0° C. until the solution was saturated.Copper (I) chloride (2.0 g, 0.020 mol) was then added to the saturated sulfur dioxide solution.The mixture was cooled to 0° C.To this mixture was added the diazonium salt solution dropwise with vigorous stirring over a period of 30 minutes.The reaction mixture was stirred at 0° C. for 1 hour and then the mixture was allowed to warm to room temperature.The mixture was stirred at room temperature for 2 h before it was poured into ice water (250 mL) and extracted with EtOAc (3*50 mL).The organics were washed with sat.NaHCO3 solution and dried over anhydrous Na2SO4.The solvent was removed in vacuo to afford an oily residue which was dissolved in tetrahydrofuran (40 mL) and cooled to 0° C.To this mixture was added a cold (0° C.) solution of ammonium hydroxide (28percent, 40 mL) portion-wise at such a rate that the internal reaction temperature was maintained below 10° C.The mixture was allowed to warm to room temperature and was then stirred at room temperature for 1 h.The solvent was removed in vacuo and the residue was dissolved in saturated aqueous sodium bicarbonate (40 mL) and washed with diethyl ether (50 mL).The aqueous layer was acidified with concentrated hydrochloric acid to pH 1.The resulting precipitate was collected by filtration and was dried under vacuum to produce of 6-Bromo-1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one (500 mg, 10percent yield).1H NMR (400 MHz, DMSO) delta 8.44 (d, J=1.5, 1H), 8.04 (dd, J=8.1, 1.5, 1H), 7.81 (d, J=8.0, 1H).

Reference： [1]Patent: US2011/98311,2011,A1

6
[ 135484-83-2 ]
[ 1223434-15-8 ]

Reference： [1]Patent: EP2565182,2013,A1
[2]Patent: US2018/215731,2018,A1

7
[ 135484-83-2 ]
[ 112253-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; at 100℃; for 12h;Sealed tube;	General procedure: The syntheses of compounds 3a-3x were mainly referred to literature method [35]. A mixture of 1a-1q, 1w, 1x (2mmol), EDC?HCl (575mg, 3mmol), HOBt (446mg, 3.3mmol), NH4Cl (348mg, 6.5mmol) and DIPEA (2.3mL, 13mmol) in DMSO (7mL) was stirred at room temperature for 15h. The mixture was extracted with EtOAc three times, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 3a-3q, 3w, 3x. A mixture of 2r-2v (2mmol) and NH3·H2O (25-28wt%, 80mmol) in sealed tube was heated at 100C for 12h. The mixture was cooled to room temperature and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 3r-3v.

Reference： [1]Patent: WO2012/13643,2012,A1
[2]European Journal of Medicinal Chemistry,2018,vol. 152,p. 235 - 252

8
[ 135484-83-2 ]
copper(l) cyanide [ No CAS ]
[ 1223434-15-8 ]

Yield	Reaction Conditions	Operation in experiment
980 mg		To an ice-cooled mixture of Compound I (1.5 g) and 2N hydrochloric acid was added a mixture of sodium nitrite (540 mg) and water (6.5 mL), and the mixture was stirred for 1 hour. The reaction mixture was neutralized by the addition of sodium carbonate. Then, to an ice-cooled mixture of copper cyanide (759 mg), potassium cyanide (637 mg), ethyl acetate (8 mL) and water (4 mL) was added the reaction mixture of Compound I which was prepared above, and the mixture was stirred for 1 hour. The reaction mixture was filtered through Celite, and to the filtrate was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 10/0 to 8/2) to give Compound II (980 mg).

Reference： [1]Patent: EP2612848,2013,A1 .Location in patent: Paragraph 0437; 0438; 0439

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Ester Cleavage ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction ? Vilsmeier-Haack Reaction

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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