[ CAS No. 38180-46-0 ] {[proInfo.proName]}

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Quality Control of [ 38180-46-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 38180-46-0 ]

SDS Specification

Alternatived Products of [ 38180-46-0 ]

Product Details of [ 38180-46-0 ]

CAS No. :	38180-46-0	MDL No. :	MFCD03788834
Formula :	C₆H₃ClN₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	YDPLFBIGFQFIDB-UHFFFAOYSA-N
M.W :	138.55	Pubchem ID :	818258
Synonyms :

Calculated chemistry of [ 38180-46-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	33.96
TPSA :	36.68 ?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) :	-6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.45
Log Po/w (XLOGP3) :	1.53
Log Po/w (WLOGP) :	1.61
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	1.98
Consensus Log Po/w :	1.39

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	0.967 mg/ml ; 0.00698 mol/l
Class :	Soluble
Log S (Ali) :	-1.91
Solubility :	1.71 mg/ml ; 0.0123 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.7
Solubility :	0.278 mg/ml ; 0.002 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 38180-46-0 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 38180-46-0 ]

* 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 [ 38180-46-0 ]
Downstream synthetic route of [ 38180-46-0 ]

[ 38180-46-0 ] Synthesis Path-Upstream 1~2

1
[ 917-64-6 ]
[ 38180-46-0 ]
[ 131109-75-6 ]

Reference： [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1990, vol. 30, # 7, p. 245 - 246
[2] Patent: WO2004/55003, 2004, A1, . Location in patent: Page 68
[3] Patent: WO2005/23807, 2005, A2, . Location in patent: Page/Page column 57
[4] Patent: US2005/215575, 2005, A1, . Location in patent: Page/Page column 19

2
[ 75-16-1 ]
[ 38180-46-0 ]
[ 131109-75-6 ]

Yield	Reaction Conditions	Operation in experiment
58 g	Stage #1: for 2 h; Cooling with ice Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.5 h; Cooling with ice	In a mixture of 54 g of 3-chloropyridine-2-carbonitrile and 300 mL of THF, 500 g of 1 M methylmagnesium bromide THF solution was added dropwise under ice cooling. The reaction mixture was stirred for 2 hours under ice cooling. The reaction mixture obtained was added to 2N hydrochloric acid under ice cooling, and the mixture was stirred for 30 minutes. A 1N sodium hydroxide aqueous solution was added to the mixture, and the mixture was adjusted to pH 8, followed by extraction with ethyl acetate. After washing the organic layer with saturated brine, the organic layer was dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain 58 g of an intermediate (12-1)
58 g	Stage #1: for 2 h; Cooling with ice Stage #2: With hydrogenchloride; water In tetrahydrofuran for 0.5 h; Cooling with ice	Preparation Example 2(1) (0639) To 3-chloropyridine-2-carbonitrile 54 g, and THF 300 mL, 1M THF solution of methyl magnesium bromide 500 mg was added dropwise under ice-cooling. The obtained reaction mixtures were stirred under ice-cooling for 2 hours. The obtained reaction mixtures were added to 2N hydrochloric acid under ice-cooling, and stirred for 30 minutes. To the mixtures was added 1N sodium hydroxide solution to adjust to pH 8, and the mixtures were extracted with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous sodium sulfate. The organic layer was concentrated to give the Intermediate compound (4-1) 58 g. ¹H-NMR (CDCl₃) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).
58 g	Stage #1: for 2 h; Cooling with ice Stage #2: With hydrogenchloride In tetrahydrofuran; water for 0.5 h; Cooling with ice	Preparation Example 12(1) To a mixture of 3-chloropyridine-2-carbonitrile 54 g and THF 300 mL was added dropwise 1M methylmagnesium bromide solution in THF 500 g under ice-cooling. The reaction mixtures were stirred under ice-cooling for 2 hours. To 2N hydrochloric acid was added the resulting reaction mixtures under ice-cooling, and the mixtures were stirred for 30 minutes. The mixtures were made pH 8 with a 1N aqueous sodium hydroxide solution, and then the mixtures were extracted with ethyl acetate. The organic layers were washed with saturated brine, and then the organic layers were dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure to give an intermediate compound (12-1) 58 g.¹H-NMR (CDCl₃) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).

58 g

Stage #1: for 2 h; Cooling with ice
Stage #2: for 0.5 h;

To a mixture of 3-chloropyridine-2-carbonitrile (54 g) and THF (300 mL) was added dropwise a 1 M solution of methylmagnesium bromide in THF (500 mL) under ice-cooling. The reaction mixture was stirred under ice-cooling for 2 hours. The resulting reaction mixture was added to 2N hydrochloric acid under ice-cooling, and the mixture was stirred for 30 minutes. To the mixture was added a 1N aqueous solution of sodium hydroxide so that the pH of the solution was set to be 8, and then the mixture was extracted with ethyl acetate. The resulting organic layers were washed with saturated brine, and then the organic layers were dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure to give the Intermediate compound 7 represented by the following formula (58 g). Intermediate compound 7: ¹H-NMR (CDCl₃) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).

Reference： [1] Patent: JP2017/36339, 2017, A, . Location in patent: Paragraph 0178
[2] Patent: US2017/295787, 2017, A1, . Location in patent: Paragraph 0639
[3] Patent: US2017/305896, 2017, A1, . Location in patent: Paragraph 0621
[4] Patent: US2019/40038, 2019, A1, . Location in patent: Paragraph 1261-1262

[ 38180-46-0 ] Synthesis Path-Downstream 1~3

1
[ 917-64-6 ]
[ 38180-46-0 ]
[ 131109-75-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; diethyl ether; at 0℃; for 2h;	Dissolve 3-CHLORO-2-CYANOPYRIDINE (10.0 g, 0.072 mol, Chem. Pharm. Bull. (1985) 33: 565-571) in anhydrous THF (200 mL) under N2 atmosphere and cool in an ice bath. Add drop wise 3.0 M MEMGI in diethyl ether (48 ml, 0.14 mol) to the reaction mixture and stir in an ice bath for 2 hours. Pour the reaction mixture over ice cold water, acidify the mixture with 2.0 N aq. HCI to pH 2 to 3. Extract the reaction mixture with EtOAc (3 x 100 mL) and dry over anhydrous MGS04. Filter, concentrate under vacuum and then filter through a pad of silica gel using 20% ethyl acetate/hexane as eluent. Removal of solvent under reduced pressure gives pure 2-acetyl-3-chloropyridine as oil
		A. [7- (3-CHLORO-PYRIDIN-2-VL)-2-METHOXYMETHVL-PYRID[2, 3-D] PYRIMIDIN-4-YL]- (L-METHVL- 123*4-TETRAHYDRO-QUINOLIN-7-YL .-AMINE (COMPOUND 1; 1. 2-ACETYL-3-CHLOROPYRIDINE; Dissolve 3-chloro-2-cyanopyridine (10.0 g, 0.072 mol, Chem. Pharm. Bull. (1985) 33: 565-571) in anhydrous THF (200 mL) under N2 atmosphere and cool in an ice bath. Add drop wise 3.0 M MEMGI in diethyl ether (48 ml, 0.14 mol) to the reaction mixture and stir in an ice bath for 2 hours. Pour the reaction mixture over ice cold water, acidify the mixture with 2.0 N aq. HCl to pH 2 to 3. Extract the reaction mixture with EtOAc (3 x 100 mL) and dry over anhydrous MGS04. Filter, concentrate under vacuum and then filter through a pad of silica gel using 20% ethyl acetate/hexane as eluent. Removal of solvent under reduced pressure gives pure 2-acetyl-3-chloropyridine as oil.
		1. 2-Acetyl-3-chloropyridine Dissolve 3-chloro-2-cyanopyridine (10.0 g, 0.072 mol, Chem. Pharm. Bull. (1985) 33:565-571) in anhydrous THF (200 mL) under N2 atmosphere and cool in an ice bath. Add drop wise 3.0 M MeMgI in diethyl ether (48 ml, 0.14 mol) to the reaction mixture and stir in an ice bath for 2 hours. Pour the reaction mixture over ice cold water, acidify the mixture with 2.0 N aq. HCl to pH 2 to 3. Extract the reaction mixture with EtOAc (3*100 mL) and dry over anhydrous MgSO4. Filter, concentrate under vacuum and then filter through a pad of silica gel using 20% ethyl acetate/hexane as eluent. Removal of solvent under reduced pressure gives pure 2-acetyl-3-chloropyridine as oil.

Reference： [1]Zeitschrift fur Chemie,1990,vol. 30,p. 245 - 246
[2]Patent: WO2004/55003,2004,A1 .Location in patent: Page 68
[3]Patent: WO2005/23807,2005,A2 .Location in patent: Page/Page column 57
[4]Patent: US2005/215575,2005,A1 .Location in patent: Page/Page column 19

2
tetrabutylammonium nitrate [ No CAS ]
[ 38180-46-0 ]
[ 488713-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic anhydride; In dichloromethane;	C. 3-Chloro-2-cyano-5-nitropyridine (775C) 3-Chloro-2-cyanopyridine (1.75 g, 12.7 mmol), tetrabutylammonium nitrate (5.02 g, 16.5 mmol), and trifluoroacetic anhydride (3.15 g, 15 mmol) were combined in 65 mL of CH2Cl2 and reacted as described in example 762C. The crude product was purified by silica gel chomatography using CH2Cl2 as the eluent to give compound 775C (0.43 g, 16%) as a pale yellow solid.

Reference： [1]Patent: US2004/77605,2004,A1

3
[ 75-16-1 ]
[ 38180-46-0 ]
[ 131109-75-6 ]

Yield	Reaction Conditions	Operation in experiment
58 g		In a mixture of 54 g of 3-chloropyridine-2-carbonitrile and 300 mL of THF, 500 g of 1 M methylmagnesium bromide THF solution was added dropwise under ice cooling. The reaction mixture was stirred for 2 hours under ice cooling. The reaction mixture obtained was added to 2N hydrochloric acid under ice cooling, and the mixture was stirred for 30 minutes. A 1N sodium hydroxide aqueous solution was added to the mixture, and the mixture was adjusted to pH 8, followed by extraction with ethyl acetate. After washing the organic layer with saturated brine, the organic layer was dried with anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain 58 g of an intermediate (12-1)
58 g		Preparation Example 2(1) (0639) To 3-chloropyridine-2-carbonitrile 54 g, and THF 300 mL, 1M THF solution of methyl magnesium bromide 500 mg was added dropwise under ice-cooling. The obtained reaction mixtures were stirred under ice-cooling for 2 hours. The obtained reaction mixtures were added to 2N hydrochloric acid under ice-cooling, and stirred for 30 minutes. To the mixtures was added 1N sodium hydroxide solution to adjust to pH 8, and the mixtures were extracted with ethyl acetate. The obtained organic layer was washed with brine and dried over anhydrous sodium sulfate. The organic layer was concentrated to give the Intermediate compound (4-1) 58 g. 1H-NMR (CDCl3) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).
58 g		Preparation Example 12(1) To a mixture of 3-chloropyridine-2-carbonitrile 54 g and THF 300 mL was added dropwise 1M methylmagnesium bromide solution in THF 500 g under ice-cooling. The reaction mixtures were stirred under ice-cooling for 2 hours. To 2N hydrochloric acid was added the resulting reaction mixtures under ice-cooling, and the mixtures were stirred for 30 minutes. The mixtures were made pH 8 with a 1N aqueous sodium hydroxide solution, and then the mixtures were extracted with ethyl acetate. The organic layers were washed with saturated brine, and then the organic layers were dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure to give an intermediate compound (12-1) 58 g.1H-NMR (CDCl3) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).

58 g		To a mixture of 3-chloropyridine-2-carbonitrile (54 g) and THF (300 mL) was added dropwise a 1 M solution of methylmagnesium bromide in THF (500 mL) under ice-cooling. The reaction mixture was stirred under ice-cooling for 2 hours. The resulting reaction mixture was added to 2N hydrochloric acid under ice-cooling, and the mixture was stirred for 30 minutes. To the mixture was added a 1N aqueous solution of sodium hydroxide so that the pH of the solution was set to be 8, and then the mixture was extracted with ethyl acetate. The resulting organic layers were washed with saturated brine, and then the organic layers were dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure to give the Intermediate compound 7 represented by the following formula (58 g). Intermediate compound 7: 1H-NMR (CDCl3) δ: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).
58 g		To a mixture of 3-chloropyridine-2-carbonitrile 54 g and THF 300 mL was added dropwise 1 M solution of methyl magnesium bromide in THF 500 mL under ice- cooling. The reaction mixture was stirred under ice-cooling for 2 hours. The resulting reaction mixture was added 2N hydrochloric acid under ice-cooling, and the mixture was stirred for 30 minutes. The mixture was made pH 8 by adding iN aqueous sodium hydroxide solution, and the mixture was then extracted with ethyl acetate. The resulting organic layers were washed with saturated brine, and the organic layers were dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure to give an intermediate compound 1 58 g. Intermediate compound 1: ‘H-NMR (CDC13) ?:8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).
58 g		10661] To a mixture of 3-chloropyridine-2-carbonitrile 54 g and THF 300 mL, 1M methylmagnesium bromide in THF solution 500 mL was added dropwise under ice-cooling. The reaction mixture was stirred under ice-cooling for 2 hours. The obtained mixture was added to 2N hydrochloric acid under ice-cooling and stirred for 30 minutes. To the mixture was added iN sodium hydroxide solution, and then the mixture was adjusted to pH 8 and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, and then the organic layer was dried over anhydrous sodium’ sulfate. The organic layer was concentrated under reduced pressure to give the intermediate compound 1 shown below 58 g.j0662] The intermediate compound 1: ‘H-NMR (CDC13) ?: 8.55 (1H, dd), 7.80 (1H, dd), 7.38 (1H, dd), 2.70 (3H, s).

Reference： [1]Patent: JP2017/36339,2017,A .Location in patent: Paragraph 0178
[2]Patent: US2017/295787,2017,A1 .Location in patent: Paragraph 0639
[3]Patent: US2017/305896,2017,A1 .Location in patent: Paragraph 0621
[4]Patent: US2019/40038,2019,A1 .Location in patent: Paragraph 1261-1262
[5]Patent: US2019/127328,2019,A1 .Location in patent: Paragraph 0587; 0588
[6]Patent: US2019/106411,2019,A1 .Location in patent: Paragraph 0661; 0662

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Technical Information

? Alkyl Halide Occurrence ? Blaise Reaction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Ritter Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Thorpe-Ziegler Reaction

Historical Records

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
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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

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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[ CAS No. 38180-46-0 ] {[proInfo.proName]}

Quality Control of [ 38180-46-0 ]

Related Doc. of [ 38180-46-0 ]

Product Details of [ 38180-46-0 ]

Calculated chemistry of [ 38180-46-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 38180-46-0 ]

Application In Synthesis of [ 38180-46-0 ]

[ 38180-46-0 ] Synthesis Path-Upstream 1~2

[ 38180-46-0 ] Synthesis Path-Downstream 1~3

Technical Information

Related Functional Groups of [ 38180-46-0 ]

Chlorides

Nitriles

Related Parent Nucleus of [ 38180-46-0 ]

Pyridines

Precautionary Statements-General

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[ 38180-46-0 ]

Related Parent Nucleus of
[ 38180-46-0 ]