Water → N-(6-chloro-5-cyanopyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748666

Reaction equation

HRID 1748666 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:17](Cl)=[O:18].[NH2:20][C:21]1[CH:22]=[C:23]([C:28]#[N:29])[C:24]([Cl:27])=[N:25][CH:26]=1.O>N1C=CC=CC=1>[Cl:27][C:24]1[N:25]=[CH:26][C:21]([NH:20][C:17]([C:3]2[CH:4]=[N:5][N:6]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][N:8]=3)[C:2]=2[CH3:1])=[O:18])=[CH:22][C:23]=1[C:28]#[N:29]

Participants

5

Reactant 3

HCID 962WaterHCID 204962095-Amino-2-chloropyridine-3-carbonitrileHCID 897349975-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride

Product 1

HCID 86692611N-(6-chloro-5-cyanopyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamideYield 195.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Methyl-1-(5-(trifluoro methyl)pyridin-2-yl)-1H-pyrazole-4-carboxylic acid chloride (200 mg) and 5-amino-2-chloro-3-cyanopyridine (228 mg) were dissolved in pyridine (10 ml) and stirred at room temperature. After completion of the reaction, water was added to the reaction solution, the precipitated solid was collected by filtration and dried under heating and blow to give N-(6-chloro-5-cyanopyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (550 mg) as a light brown solid.

Workup

  1. additionwas added to the reaction solution
  2. filtrationthe precipitated solid was collected by filtration
  3. customdried
  4. temperatureunder heating

Sources & evidence

ORD record
ord-79ace4301b51486bb49e09edddddf152
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Linked notes

Loading…