[ CAS No. 39853-81-1 ] {[proInfo.proName]}

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Quality Control of [ 39853-81-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 39853-81-1 ]

Product Details of [ 39853-81-1 ]

CAS No. :	39853-81-1	MDL No. :	MFCD09953461
Formula :	C₇H₅Cl₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	190.03	Pubchem ID :	-
Synonyms :

Safety of [ 39853-81-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 39853-81-1 ]

* 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 [ 39853-81-1 ]
Downstream synthetic route of [ 39853-81-1 ]

[ 39853-81-1 ] Synthesis Path-Upstream 1~2

1
[ 39853-81-1 ]
[ 39745-40-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 10, p. 2993 - 3006

2
[ 67-56-1 ]
[ 39853-81-1 ]
[ 53277-47-7 ]

Reference： [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 6, p. 996 - 1001

[ 39853-81-1 ] Synthesis Path-Downstream 1~8

1
[ 38116-61-9 ]
[ 39853-81-1 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2993 - 3006

2
[ 39853-81-1 ]
[ 4795-29-3 ]
2-chloro-6-methyl-N-[(2S)-tetrahydro-2-furanylmethyl]nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; for 4h;	EXAMPLE 125 2-chloro-6-methyl-N-[(2S)-tetrahydro-2-furanylmethyl]nicotinamide A suspension of 2-chloro-6-methylnicotinic acid (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0 C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of (2S)-tetrahydro-2-furanylmethylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 255.0 (M+H)+; 1H NMR (DMSO-d6) delta 1.56-1.67 (m, 1H), 1.76-1.99 (m, 3H), 2.47 (s, 3H), 3.22-3.35 (m, 2H), 3.59-3.66 (m, 1H), 3.74-3.81 (m, 1H), 3.90-3.97 (m, 1H), 7.32 (d, 1H), 7.72 (d, 1H), 8.55 (t, 1H).

Reference： [1]Patent: US2004/67985,2004,A1 .Location in patent: Page/Page column 25-26

3
[ 39853-81-1 ]
[ 7202-43-9 ]
[ 676534-26-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane for 4h;	126 2-chloro-6-methyl-N-[(2R)-tetrahydro-2-furanylmethyllnicotinamide EXAMPLE 126 2-chloro-6-methyl-N-[(2R)-tetrahydro-2-furanylmethyllnicotinamide A suspension of 2-chloro-6-methylnicotinic acid (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0° C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of (2R)-tetrahydro-2-furanylmethylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 255.0 (M+H)+; 1H NMR (DMSO-d6) δ 1.55-1.67 (m, 1H), 1.77-1.97 (m, 3H), 2.47 (s, 3H), 3.21-3.36 (m, 2H), 3.59-3.68 (m, 1H), 3.74-3.81 (m, 1H), 3.90-3.97 (m, 1H), 7.32 (d, 1H), 7.72 (d, 1H), 8.55 (t, 1H).

Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US2004/67985, 2004, A1 Location in patent: Page/Page column 26

4
[ 67-56-1 ]
[ 39853-81-1 ]
[ 53277-47-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 996 - 1001

5
[ 30529-70-5 ]
[ 39853-81-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In dichloromethane; at 0℃; for 1h;	A suspension of <strong>[30529-70-5]2-chloro-6-methylnicotinic acid</strong> (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0 C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of sec-butylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 227.1 (M+H)+; 1H NMR (DMSO-d6) delta 0.90 (t, 3H), 1.11 (d, 3H), 1.43-1.51 (m, 2H), 2.47 (s, 3H), 3.80-3.83 (m, 1H), 7.31 (d, 1H), 7.72 (d, 1H), 8.26 (d, 1H).; A suspension of <strong>[30529-70-5]2-chloro-6-methylnicotinic acid</strong> (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0 C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of pentylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 241.0 (M+H)+; 1H NMR (DMSO-d6) delta 0.85-0.92 (m, 3H), 1.27-1.36 (m, 4H), 1.45-1.56 (m, 2H), 2.47 (s, 3H), 3.17-3.24 (m, 2H), 7.32 (d, 1H), 7.73 (d, 1H), 8.43 (t, 1H).; A suspension of <strong>[30529-70-5]2-chloro-6-methylnicotinic acid</strong> (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0 C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of 2-methylbutylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 241.0 (M+H)+; 1H NMR (DMSO-d6) 0.82-0.95 (m, 6H), 1.09-1.21 (m, 1H), 1.37-1.49 (m, 1H), 1.54-1.66 (m, 1H), 2.47 (s, 3H), 2.99-3.08 (m, 1H), 3.11-3.19 (m, 1H), 7.32 (d, 1H), 7.73 (s, 1H). 8.43 (t, 1H).; A suspension of <strong>[30529-70-5]2-chloro-6-methylnicotinic acid</strong> (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0 C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of 2-ethoxyethylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 243.0 (M+H)+; 1H NMR (DMSO-d6) delta 1.12 (t, 3H), 2.47 (s, 3H), 3.37 (q, 2H), 3.43-3.51 (m, 4H), 7.32 (d, 1H), 7.73 (d, 1H), 8.53 (t, 1H).; A suspension of <strong>[30529-70-5]2-chloro-6-methylnicotinic acid</strong> (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0 C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of 3-propoxypropylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 271.0 (M+H)+; 1H NMR (DMSO-d6) delta 0.86 (t, 3H), 1.36-1.46 (m, 2H), 1.68-1.77 (m, 2H), 2.47 (s, 3H), 3.24-3.34 (m, 4H), 3.43 (t, 2H), 7.32 (d, 1H), 7.74 (d, 1H), 8.44 (t, 1H).; A suspension of <strong>[30529-70-5]2-chloro-6-methylnicotinic acid</strong> (6 mmol) in dry dichloromethane (9 mL) was treate...
	With oxalyl dichloride; In dichloromethane; at 0℃; for 2h;	To the solution of <strong>[30529-70-5]2-chloro-6-methylnicotinic acid</strong> (5 g, 29.1 mmol) in CH2C12 (40 mL) was added oxalyl dichloride (8.1 g, 63.8 mmol) at 0 C and the reaction mixture was stirred for 2 h. The mixture was concentrated and 40 mL of methanol was then added at 0 C and the reaction mixture was stirred at RT for 12 h. The mixture was then concentrated in vacuo and extracted with EtOAc. The combined organic layers were washed with brine, dried ove a2S04, filtered, and concentrated in vacuo to provide methyl 2-chloro-6-methylnicotinate that is used without further purification as a light yellow solid

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 996 - 1001
[2]Patent: US2004/67985,2004,A1 .Location in patent: Page/Page column 24-27
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 2137 - 2146
[4]Patent: WO2015/35113,2015,A1 .Location in patent: Page/Page column 78; 79

6
[ 39853-81-1 ]
[ 39745-40-9 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2993 - 3006

7
[ 326816-37-9 ]
[ 39853-81-1 ]
[ 743456-22-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium carbonate In acetonitrile at 20℃; for 72h;	B Example B : Preparation of 2-Chloro-N-[2-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-ethyl]-6-methyl-nicotinamide A solution of 161 mg (0.7 mmol) 2-chloro-6-methylnictotinyl chloride, 160 mg (0.7 mmol) 2-(3-chloro-5-trifluormethyl-pyridin-2-yl)-ethylamine hydrochloride and 236 mg (1.7 mmol) sodium carbonate in 8 ml acetonitrile is stirred for 3 days at room temperature. The mixture is diluted with 5ml water and 5 ml ethylacetate, separated and the organic phase is washed with sat. NH4Cl solution and water. The organic phase is dried over sodium sulfate and evaporated. Yield: 200 mg (62%).

Reference： [1]Current Patent Assignee: BAYER AG - EP1449841, 2004, A1 Location in patent: Page 31

8
[ 6850-35-7 ]
[ 39853-81-1 ]
2-chloro-6-methyl-N-(3-methylcyclohexyl)nicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane for 4h;	131 2-chloro-6-methyl-N-(3-methylcyclohexyl)nicotinamide EXAMPLE 131 2-chloro-6-methyl-N-(3-methylcyclohexyl)nicotinamide A suspension of 2-chloro-6-methylnicotinic acid (6 mmol) in dry dichloromethane (9 mL) was treated with thionyl chloride (12.4 mmol) at 0° C., stirred for one hour, and concentrated in vacuo. The concentrate was added dropwise to a cold solution of 3-methylcyclohexylamine (6 mmol) and triethylamine (4.5 mL) in dichloromethane (20 mL). The mixture was stirred for 4 hours and then concentrated in vacuo. The residue was dissolved in dichloromethane, washed sequentially with saturated sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by HPLC on a C-18 column using a solvent system increasing in gradient from 5% to 100% acetonitrile/water containing 0.01% TFA over 50 minutes to provide the desired product as the trifluoroacetate salt. MS m/e 267 (M+H)+; 1H NMR (DMSO-d6) δ 0.73-0.84 (m, 0.65H), 0.85-0.93 (m, 3.35H), 0.97-1.05 (m, 0.35H), 1.06-1.16 (m, 0.65H), 1.22-1.37 (m, 1H), 1.39-1.75(m, 4H), 1.77-1.89 (m, 2H), 2.47 (d, 3H), 3.64-3.74 (m, 0.65H), 4.07 (br s, 0.35H), 7.30 (d, 1H), 7.71 (d, 1H), 8.32 (d, 1H).

Reference： [1]Current Patent Assignee: ABBOTT LABORATORIES INC - US2004/67985, 2004, A1 Location in patent: Page/Page column 27

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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

[ CAS No. 39853-81-1 ] {[proInfo.proName]}

Quality Control of [ 39853-81-1 ]

Related Doc. of [ 39853-81-1 ]

Product Details of [ 39853-81-1 ]

Safety of [ 39853-81-1 ]

Application In Synthesis of [ 39853-81-1 ]

[ 39853-81-1 ] Synthesis Path-Upstream 1~2

[ 39853-81-1 ] Synthesis Path-Downstream 1~8

Precautionary Statements-General

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