[ CAS No. 5350-93-6 ] {[proInfo.proName]}

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Quality Control of [ 5350-93-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5350-93-6 ]

SDS Specification

Alternatived Products of [ 5350-93-6 ]

Product Details of [ 5350-93-6 ]

CAS No. :	5350-93-6	MDL No. :	MFCD00006243
Formula :	C₅H₅ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QAJYCQZQLVENRZ-UHFFFAOYSA-N
M.W :	128.56	Pubchem ID :	79305
Synonyms :

Calculated chemistry of [ 5350-93-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	33.65
TPSA :	38.91 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.18
Log Po/w (XLOGP3) :	1.09
Log Po/w (WLOGP) :	1.33
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	1.37
Consensus Log Po/w :	1.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.88
Solubility :	1.7 mg/ml ; 0.0132 mol/l
Class :	Very soluble
Log S (Ali) :	-1.5
Solubility :	4.07 mg/ml ; 0.0317 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.24
Solubility :	0.735 mg/ml ; 0.00571 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 5350-93-6 ]

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

Application In Synthesis of [ 5350-93-6 ]

* 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 [ 5350-93-6 ]
Downstream synthetic route of [ 5350-93-6 ]

[ 5350-93-6 ] Synthesis Path-Upstream 1~2

1
[ 5350-93-6 ]
[ 123-63-7 ]
[ 764717-61-5 ]

Reference： [1] Yakugaku Zasshi, 1945, vol. 65, p. Ausg. B, S. 532[2] Chem.Abstr., 1952, p. 110

2
[ 5350-93-6 ]
[ 52382-48-6 ]

Reference： [1] European Journal of Inorganic Chemistry, 1999, # 9, p. 1507 - 1521
[2] Synthetic Communications, 1999, vol. 29, # 19, p. 3341 - 3352
[3] Journal of the American Chemical Society, 2016, vol. 138, # 48, p. 15790 - 15796

[ 5350-93-6 ] Synthesis Path-Downstream 1~12

1
[ 4318-78-9 ]
[ 5350-93-6 ]
2-(6-chloro-[3]pyridylazo)-pyridine-3,5-diyldiamine [ No CAS ]

Reference： [1]Patent: DE617187,1934,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 22,p. 470

2
[ 5350-93-6 ]
[ 123-63-7 ]
[ 764717-61-5 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1945,vol. 65,p. Ausg. B, S. 532
Chem.Abstr.,1952,p. 110

3
[ 5350-93-6 ]
[ 400777-00-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1233 - 1236
[2]Patent: US8426450,2013,B1
[3]Patent: WO2015/148344,2015,A2
[4]Patent: US9403772,2016,B2
[5]Inorganic Chemistry,2017,vol. 56,p. 8381 - 8389

4
[ 5350-93-6 ]
[ 171178-47-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226

5
[ 5350-93-6 ]
[ 58483-95-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 256 - 261
[3]Patent: WO2008/130021,2008,A2

6
[ 5350-93-6 ]
[ 171178-46-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226
[2]Patent: WO2008/76425,2008,A1
[3]Patent: WO2008/130600,2008,A2
[4]Patent: WO2008/130021,2008,A2
[5]Patent: WO2020/20939,2020,A1

7
[ 5350-93-6 ]
[ 464213-92-1 ]
[ 37091-73-9 ]
N-(6-chloropyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;	Example 131 N-(6-Chloropyridin-3-yl)-4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide 2-Chloro-1,3-dimethylimidazolinium chloride (61 mg, 0.361 mmol), 5-amino-2-chloropyridine (46 mg, 0.361 mmol) and triethylamine (36 mg, 0.361 mmol) were added to a methylene chloride solution (3 ml) of 4-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (45 mg, 0.120 mmol) in a nitrogen atmosphere and the resulting solution was stirred all the night through. The reaction solution was diluted with chloroform, then washed with water and dried, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3:1) to obtain the titled compound (10 mg, 0.021 mmol, 17percent).

Reference： [1]Patent: EP1314712,2003,A1

8
[ 5350-93-6 ]
[ 464213-93-2 ]
[ 37091-73-9 ]
N-(6-chloropyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;	Example 184 N-(6-Chloropyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide 5-Amino-2-chloropyridine (0.206 g, 1.604 mmol), triethylamine (0.162 g, 1.604 mmol) and <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong> (0.271 g, 1.604 mmol) were added to a methylene chloride solution (100 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.200 g, 0.535 mmol) and the resulting solution was stirred at room temperature for 10 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform: methanol = 10:1) and then recrystallized from ether to obtain the titled compound (0.142 g, 0.293 mmol, 55percent).

Reference： [1]Patent: EP1314712,2003,A1

9
[ 5350-93-6 ]
[ 6967-82-4 ]
[ 1119088-90-2 ]

Yield	Reaction Conditions	Operation in experiment
46%	With copper(I) oxide; copper; potassium carbonate; In 1,2-dimethoxyethane; at 130℃; for 16h;	Intermediate 13; 2-(6-Chloropyridin-3-ylamino)-5-methylbenzoic acid A mixture of 6-ch.oropyridin-3-amine (11.67 mmol, 1.5 g) and 2-bromn-5-methylbenzoic acid (23.34 mmol, 5.02 g), Cu (1.17 mmol, 0.1 g), Cu2O (0.58 mmol, 0.1 g) and K2CO3 (23.34 mmol, 3.2 g) in 1 ,2-dimethoxyethane (15 ml) was heated at 13O0C for 16 hours, under argon atmosphere. Water was added and the mixture was filtered through celite. HCI 2N aqueous solution was added until pH 6 and the solid formed was filtered off. The crude was purified by chromatography eluting with DCM/MeOH mixtures affording 1.40 g (yield 46%).1H NMR (DMSO-de) delta ppm: 2.24 (s, 3H), 7.16-7.19 (d, 1 H), 7.25-7.27 (d, 1 H), 7.38- 7.41 (d, 1 H), 7.67-7.73 (m, 2H), 8.28 (s, 1 H), 9.45 (bs, 1 H).ESI/MS (m/e, %): 263 [(M+1)+, 100].

Reference： [1]Patent: WO2009/21696,2009,A1 .Location in patent: Page/Page column 49

10
[ 5350-93-6 ]
[ 1050501-88-6 ]

Yield	Reaction Conditions	Operation in experiment
99.8%		Step 1: synthesis of 2-bromo-6-chloropyridin-3-amine 11-aBromine (24.86 g, 155.57 mmol) was added to a solution of 6-chloropyridin-3 -amine (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid (383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acid was then evaporated. The residue was dissolved in EtOAc, washed with saturated aqueous Na2C03, water and brine. The organic layer was dried over MgS04, filtered and evaporated, yielding 32.20 g of the desired product 11-a (99.8%). m/z = 206.96 (M+H)+, Cl+Br pattern.
99.8%	With bromine; sodium acetate; acetic acid; at 20℃; for 1h;	Bromine (24.86 g, 155.57 mmol) was added to a solution of 6-chloropyridin-3 -amine 28-a (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid (383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acid was then evaporated. The residue was dissolved in EtOAc, washed with saturated aqueous Na2C03, water and brine. The organic layer was dried over MgSC^, filtered and evaporated, yielding 32.20 g of the desired intermediate 28-b (99.8%).
99.8%	With bromine; sodium acetate; acetic acid; at 20℃; for 1h;	Bromine (24.86 g, 155.57 mmol) was added to a solution of6-chloropyridin-3-amine (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid(383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acidwas then evaporated. The residue was dissolved in EtOAc, washed with saturatedaqueous Na2C03, water and brine. The organic layer was dried over MgS04, filteredand evaporated, yielding 32.20 g of the desired product 49-a (99.8%). m/z = 206.96 (M+ It

99.8%	With bromine; sodium acetate; acetic acid; at 25℃; for 1h;	Step 1: synthesis of 2-bromo-6-chloropyridin-3-amine (intermediate 20a)Bromine (24.86 g, 155.57 mmol) was added to a solution of 6-chloropyridin-3-amine(20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid(383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acidwas then evaporated. The residue was dissolved in EtOAc, washed with saturatedaqueous Na2CO3, water and brine. The organic layer was dried over MgSO4, filteredand evaporated, yielding 32.20 g of the desired product 20a (99.8%). m/z = 206.96 (M+H), Cl+Br pattern.
99.8%	With bromine; sodium acetate; acetic acid; In ethyl acetate; at 20℃; for 1h;	Bromine (24.86 g, 155.57 mmol) was added to a solution of 6-chloropyridin-3-amine (20.00 g, 155.57 mmol) and sodium acetate (25.52 g, 311.14 mmol) in acetic acid (383 ml). The reaction mixture was stirred at room temperature for 1 hour. Acetic acid was then evaporated. The residue was dissolved in EtOAc, washed with saturated aqueous Na2CO3, water and brine. The organic layer was dried over MgSO4, filtered and evaporated, yielding 32.20 g of the desired product 49-a (99.8%). m/z=206.96 (M+1)+
	With bromine; sodium acetate; acetic acid; at 20℃; for 18h;	To a mixture of 6-chloropyridin-3-amine (5 g, 38.9 mmol) and NaOAc (6.37 g, 77.8 mmol) in AcOH (30 mL) was added a solution of bromine (6.8 g, 42.8 mmol) in AcOH(5 mL) . The resulting reaction mixture was stirred at room temperature for 1 8hrs. Acetic acid was removed under reduced pressure to give the residue, which was dissolved into EA (50 mL), washed by NaHCO3 aqueous (20 mL x 5), water and brine. The organic layers was dried over Na2SO4, and the drying agent was filtered off. The filtrate was concentrated in vavuo to give the crude product, which was purified by silica gel chromatography (silica gel, eluting with 5% methanol in DCM) to give (5 g, 62%) as an orange solid. HPLC/UV purity: 90%; LC-MS (ESI): 207.3 (M + 1).

Reference： [1]Patent: WO2012/80450,2012,A1 .Location in patent: Page/Page column 25
[2]Patent: WO2013/186335,2013,A1 .Location in patent: Page/Page column 87
[3]Patent: WO2013/186333,2013,A1 .Location in patent: Page/Page column 102
[4]Patent: WO2014/60411,2014,A1 .Location in patent: Page/Page column 56
[5]Patent: US2015/111868,2015,A1 .Location in patent: Paragraph 0856; 0857
[6]Organic Process Research and Development,2012,vol. 16,p. 1069 - 1081
[7]Patent: WO2018/204176,2018,A1 .Location in patent: Paragraph 00471

11
[ 5350-93-6 ]
[ 17823-69-7 ]
[ 1456732-75-4 ]

Yield	Reaction Conditions	Operation in experiment
		Dissolved 0.500 g <strong>[17823-69-7]2-cyano-3,3-bis(methylthio)acrylamide</strong> in 15 mL EtOH and added 5-amino-2-chloropyridine (1.0 eq.) . Stirred reaction at 75 C until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75 C until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain a yellow powder as product. Product was allowed to dry under vacuum for 1 hr. 5-amino-3-((6-chloropyridin-3-yl)amino)-lH-pyrazole-4-carboxamide

Reference： [1]Patent: WO2013/138613,2013,A1 .Location in patent: Paragraph 00423

12
[ 5350-93-6 ]
[ 24424-99-5 ]
[ 171178-46-4 ]

Reference： [1]Patent: WO2015/200534,A2
Patent: ,2015,
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 256 - 261

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

Historical Records

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[ 5350-93-6 ]

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Ghs Precautionary Statements

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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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[ CAS No. 5350-93-6 ] {[proInfo.proName]}

Quality Control of [ 5350-93-6 ]

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Product Details of [ 5350-93-6 ]

Calculated chemistry of [ 5350-93-6 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 5350-93-6 ]

Application In Synthesis of [ 5350-93-6 ]

[ 5350-93-6 ] Synthesis Path-Upstream 1~2

[ 5350-93-6 ] Synthesis Path-Downstream 1~12

Technical Information

Related Functional Groups of [ 5350-93-6 ]

Chlorides

Amines

Related Parent Nucleus of [ 5350-93-6 ]

Pyridines

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[ 5350-93-6 ]

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[ 5350-93-6 ]