Dichloromethane → N-{6-[1-(Dimethylcarbamoyl)-1,2,3,6-tetrahydropyridin-4-yl]-5-methylpyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748676Notes

Reaction equation

HRID 1748676 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:13])[C:10](Cl)=[O:11].[CH3:14][C:15]1[N:19]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=2)[N:18]=[CH:17][C:16]=1[C:30]([NH:32][C:33]1[CH:34]=[N:35][C:36]([C:40]2[CH2:41][CH2:42][NH:43][CH2:44][CH:45]=2)=[C:37]([CH3:39])[CH:38]=1)=[O:31].ClCCl>C(O)C.O>[CH3:8][N:9]([CH3:13])[C:10]([N:43]1[CH2:44][CH:45]=[C:40]([C:36]2[N:35]=[CH:34][C:33]([NH:32][C:30]([C:16]3[CH:17]=[N:18][N:19]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=4)[C:15]=3[CH3:14])=[O:31])=[CH:38][C:37]=2[CH3:39])[CH2:41][CH2:42]1)=[O:11]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6598Dimethylcarbamoyl ChlorideHCID 8471Triethylamine2×HCID 866925385-Methyl-N-[5-methyl-6-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Product 1

HCID 86692623N-{6-[1-(Dimethylcarbamoyl)-1,2,3,6-tetrahydropyridin-4-yl]-5-methylpyridin-3-yl}-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Triethylamine (33 μl) and dimethylcarbamoyl chloride (22 μl) were added to a mixture of 5-methyl-N-[5-methyl-6-(1,2,3,6-tetrahydropyridin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (100 mg) and dichloromethane (4.6 ml) and stirred at room temperature for two hours. Triethylamine (95 μl), water and ethanol were added to the reaction solution and the solvent was evaporated in vacuo. The precipitated solid was washed with water and ethanol to give the titled compound (66 mg) as a white solid.

Workup

  1. customthe solvent was evaporated in vacuo
  2. washThe precipitated solid was washed with water and ethanol

Sources & evidence

ORD record
ord-d68734c3421445099dcc6acbf6a14b99
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

Loading…