[ CAS No. 1074-82-4 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 1074-82-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1074-82-4 ]

SDS Specification

Alternatived Products of [ 1074-82-4 ]

Product Details of [ 1074-82-4 ]

CAS No. :	1074-82-4	MDL No. :	MFCD00005887
Formula :	C₈H₄KNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FYRHIOVKTDQVFC-UHFFFAOYSA-M
M.W :	185.22	Pubchem ID :	3356745
Synonyms :

Calculated chemistry of [ 1074-82-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.86
TPSA :	34.14 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-8.96
Log Po/w (XLOGP3) :	1.15
Log Po/w (WLOGP) :	0.97
Log Po/w (MLOGP) :	1.65
Log Po/w (SILICOS-IT) :	1.55
Consensus Log Po/w :	-0.73

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.08
Solubility :	1.53 mg/ml ; 0.00826 mol/l
Class :	Soluble
Log S (Ali) :	-1.46
Solubility :	6.4 mg/ml ; 0.0346 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.76
Solubility :	0.325 mg/ml ; 0.00175 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.1

Safety of [ 1074-82-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1074-82-4 ]

* 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 [ 1074-82-4 ]
Downstream synthetic route of [ 1074-82-4 ]

[ 1074-82-4 ] Synthesis Path-Upstream 1~1

1
[ 1252018-10-2 ]
[ 1074-82-4 ]
[ 446292-07-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	at 20 - 100℃; for 3 h;	Example 3:Preparation of 2-((2R)-2-Hydroxy-3-[4-(3-oxomorpholin-4-yl)- phenyl]amino}proply)-1 /-/-isoindole-1 ,3(2H)-dione (7a): Potassium phthalimide (7.16 g, 38.632 mmoL) was added in one portion to a mechanically stirred mixture of 4-[4-(N-(3-chloro-2R-hydroxy-1-propyl)amino)phenyl]morpholin-3- one (10 g, 35.119 mmoL) in DMF (60 mL). The suspension was stirred at room temperature and was heated to 100 °C, stirred at that temperature for 3 h and then cooled to room temperature. Water (60 mL) was charged and the suspension stirred for another 15 min. The suspension was filtered through a Buchner funnel. The solid was washed with water (2 x 40 mL) and dried under vacuum at 50°C for 10 h to yield 2-((2f?)-2-Hydroxy-3-[4-(3-oxomorpholin-4- yl)-phenyl]amino}proply)-1 7-isoindole-1 ,3(2/-/)-dione (12.55 g, 93percent) as a crystalline white solid.¹HNMR (400MHz, DMSO-d6) δ 2.99-3.05 (m, 1 H), 3.14-3.2 (m, 1 H), 3.59-3.69 (m, 4H), 3.91-3.94 (m, 2H), 3.97-4.05 (m, 1 H), 4.14 (s, 2H), 5.16 (d, J=5.2 Hz, 1 H), 5.66 (t, J=6.0 Hz, 1 H), 6.61 (d, J=8.7 Hz, 2H), 7.03 (d, J=8.8 Hz, 2H), 7.82-7.88 (m, 4H).
92%	Stage #1: With sodium hydroxide In dichloromethane; water at 20℃; for 8 h; Stage #2: at 100℃; for 3 h;	The above 57.6 g of intermediate 4 and 400 mL of dichloromethane were charged into a 1 L three-necked flask,A solution of 17.8 g of Na0H and 60 mL of water was added dropwise at room temperature,After stirring at room temperature for 6 h, the organic layer was washed with 120 mL of water and then with 60 mL of saturated brine,The organic layer was dried over anhydrous sodium sulfate,Filtered, concentrated to 180mL of liquid, by adding 360mL n-hexane heated reflux 30min,System cooling to room temperature and then stirring 2h,The filter cake was washed with dichloromethane and n-hexane (1: 3)The filter cake was dried in vacuo for 12 h to give 48.2 g of white crystals.48 g (0.17 mol) of the above solid and 240 mL of the 4-dioxane were charged into a 500 mL three-necked flask,34.4 g (0.19 mol) of potassium phthalimide potassium salt was added with stirring,System gradually heated to 100 ° C, stirring 3h, cooling to room temperature, add 60mL water stirring 15min,Filter, filter cake washed with 2X1 OOmL,White crystals were obtained at 50 ° C in vacuum and dried 1 Oh to give 60.2 g of compound 6 (92percent) mp. = 211.7-211.9 ° C.
87.8%	for 10 h; Reflux	The reaction flask, and the resulting 32.7g (0.115mol) of intermediate V with 300ml of anhydrous methanol was dissolved, followed by addition of 29.1g (0.157mol) of potassium phthalimide and heated at reflux for 9 hours, TLC in the control (ethyl acetate: methanol = 10: 1, volume ratio) to complete the reaction, filtered hot, the filtrate was lowered to room temperature (about 25 ) was stirred for 2 hours, filtered, the filter cake was rinsed with 75ml of anhydrous methanol, and drying under reduced pressure, intermediate VI to give an off-white about 39.9g (0.101mol), intermediate V molar yield intermediate VI is prepared from about 87.8percent.

87.8%	for 9 h; Reflux	In the reaction flask, the obtained 32.7 g (0.115 mol) of the intermediate V was dissolved with 300 ml of anhydrous methanol,Then, 29.1 g (0.157 mol) of potassium phthalimide was added and the mixture was heated to reflux for 9 hours.The reaction was completed by TLC (ethyl acetate:methanol=10:1, volume ratio) and the reaction was complete. The filtrate was cooled to room temperature (about 25° C.) and stirred for 2 hours. The mixture was filtered, and the filter cake was rinsed with 75 ml of anhydrous methanol. drying,About 39.9 g (0.101 mol) of the off-white intermediate VI was obtained, and about 87.8percent of the intermediate V was produced in the molar yield of the intermediate VI.
51.4 g	for 10 h; Reflux	In the reaction flask, the obtained 42.6 g (0.15 mol)Intermediate V was dissolved with 400 ml anhydrous methanol.Then 38.8 g (0.21 mol) of potassium phthalimide was added,The mixture was heated at reflux for 10 hours, and the reaction was completed by TLC (ethyl acetate: methanol = 10:1, volume ratio).Heat filtered, the filtrate was cooled to room temperature (about 25°C) and stirred for 2 hours, filtered,The filter cake was rinsed with 100 ml of anhydrous methanol and dried under reduced pressure to obtain about 51.4 g (0.13 mol) of the off-white intermediate VI. The intermediate V produced the intermediate VI in a molar yield of about 86.7percent.

Reference： [1] Patent: WO2012/51692, 2012, A1, . Location in patent: Page/Page column 42-43
[2] Patent: CN103951661, 2017, B, . Location in patent: Paragraph 0043-0044
[3] Patent: CN104974105, 2017, B, . Location in patent: Paragraph 0073
[4] Patent: CN104974149, 2018, B, . Location in patent: Paragraph 0074; 0075; 0077; 0081; 0083
[5] Patent: WO2012/32533, 2012, A2, . Location in patent: Page/Page column 15
[6] Patent: CN104974148, 2017, B, . Location in patent: Paragraph 0073; 0074; 0076; 0082

[ 1074-82-4 ] Synthesis Path-Downstream 1~14

1
[ 558-42-9 ]
[ 1074-82-4 ]
[ 167108-05-6 ]

Yield	Reaction Conditions	Operation in experiment
37%	With sodium iodide; In N,N-dimethyl-formamide;Heating / reflux;	A solution of 1-chloro-2-methyl-2-propanol (2.23 g, 97percent, 0.02 mol), potassium phthalimide (3.780 g, 98percent, 0.02 mol) and sodium iodide (60 mg, 4 mmol) in anhydrous DMF (40 mL) was heated to reflux overnight. The solvent was evaporated under reduced pressure. The resulting product was triturated with a mixture of 3:2 ethyl acetate/hexanes and the ensuing white precipitate was removed by filtration. The yellow filtrate was concentrated under reduced pressure and purified by flash chromatography in a mixture of 2:3 ethyl acetate/hexanes. The impure product thus isolated was triturated with hot hexanes (125 mL) and filtered to remove an insoluble white impurity. After evaporation of the solvent under reduced pressure, the obtained white solid was recrystallized in hexanes. The product was yielded as colorless crystals that were collected by filtration and dried under high vacuum (1.63 g, 37percent yield). m.p.: 104-105° C.; TLC Rf 0.20 (2:3 ethyl acetate/hexanes); FTIR (KBr): 3524, 3456, 3097, 3031, 2973, 2930, 1773, 1698, 1611, 1466, 1427, 1389, 1319, 1190, 1076, 990, 965, 912, 890, 838, 766, 724, 712, 638 cm-1; 1H-NMR(500 MHz, CDCl3): delta 1.26 (s, 6H, 2 CH3), 2.74 (s, 1H, OH), 3.75 (s, 2H, CH2), 7.72 (dd, 2H, Jo=5.44 Hz, Jm=3.04 Hz, 2 Hc),, 7.85 (dd, 2H, Jo=5.42 Hz, Jm=3.06 Hz, 2 Hb); 13C-NMR(126 MHz, CDCl3): delta 27.6 (2 CH3), 49.3 (CH2), 71.6 (CMe2), 123.6 (2 Cb), 132.0 (2 Ca), 134.3 (2 Cc), 169.3 (2 CO).

Reference： [1]Patent: US2008/102028,2008,A1 .Location in patent: Page/Page column 9; 10
[2]Chemische Berichte,1921,vol. 54,p. 3160

2
[ 34270-90-1 ]
[ 1074-82-4 ]
[ 43113-25-3 ]

Reference： [1]Chemische Berichte,1905,vol. 38,p. 3413

3
[ 10226-29-6 ]
[ 1074-82-4 ]
[ 71510-41-3 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 2067 - 2074

4
[ 439134-78-8 ]
[ 1074-82-4 ]
[ 929693-86-7 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 685 - 695

5
[ 1074-82-4 ]
[ 103347-14-4 ]
[ 169045-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide;	PREPARATION 91(3) To a solution of <strong>[103347-14-4]4-chloro-3-methoxybenzyl bromide</strong> (7.00 g) in anhydrous dimethylformamide (50 mL) was added potassium phthalimide (6.03 g), and the mixture was stirred for 2 hours at ambient temperature. The mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give N-(4-chloro-3-methoxybenzyl)phthalimide as white powders (5.88 g). NMR (CDCl3, delta): 3.90 (3H, s), 4.80 (2H, s), 6.96 (1H, d, J=8 Hz), 7.05 (1H, s), 7.25-7.31 (1H, m), 7.68-7.75 (2H, m), 7.82-7.90 (214, m).

Reference： [1]Patent: US6384080,2002,B1

6
[ 20587-30-8 ]
[ 1074-82-4 ]
[ 161292-80-4 ]

Yield	Reaction Conditions	Operation in experiment
33%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;	1 Methyl 5-phthalimidomethyl-2-nitrobenzoate A mixture of <strong>[20587-30-8]methyl 5-methyl-2-nitrobenzoate</strong> (35.0 g, 179 mmol), N-bromosuccinimide (33.5 g, 188 mmol), and azobisisobutyronitrile (500 mg) in carbon tetrachloride (450 mL) was refluxed for 14 h. The insoluble material formed was removed by filtration and the filtrate was concentrated. The residue was dissolved in DMF (300 mL) and potassium phthalimide (19.41 g, 45 mmol) was added. The mixture was stirred for 2 h at 50 C., poured into brine, and extracted with a 1:1 mixture of toluene and ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 4:1 to 2:1 hexane/ethyl acetate to give 20.0 g of the title compound (33%). 1 H NMR (CDCl3) delta7.85~7.92 (m, 3H), 7.73~7.80 (m, 3H), 7.68 (dd, 1H, J=8.2, 2.0 Hz), 4.92 (s, 2H), 3.91 (s, 3H).

Reference： [1]Patent: US5719152,1998,A

7
[ 4018-65-9 ]
[ 70987-78-9 ]
[ 1074-82-4 ]
[ 98-59-9 ]
C₁₇H₁₂ClNO₄ [ No CAS ]