Pyridine → N-(2-chloropyrimidin-5-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748688Notes

Reaction equation

HRID 1748688 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=2)[N:12]=[CH:11][C:10]=1[C:24](Cl)=[O:25].[N:27]1C=CC=CC=1.[NH2:33][C:34]1[CH:35]=C[C:37]([Cl:40])=[N:38][CH:39]=1>O>[Cl:40][C:37]1[N:27]=[CH:35][C:34]([NH:33][C:24]([C:10]2[CH:11]=[N:12][N:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=3)[C:9]=2[CH3:8])=[O:25])=[CH:39][N:38]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 793055-Amino-2-chloropyridineHCID 897349975-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride

Product 1

HCID 86692639N-(2-chloropyrimidin-5-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Toluene (5 ml) was added to 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride (500 mg) described in Reference Example 180, pyridine (5 ml) and 5-amino-2-chloropyridine (198 mg) were added thereto with stirring, and the mixture was stirred at 80° C. for two hours. After completion of the reaction, water was added to the reaction solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) to give N-(2-chloropyrimidin-5-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (410 mg) as a white solid.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at 80° C. for two hours
  3. additionwas added to the reaction solution
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-193394df043047bcb842cd98228ef49b
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

Loading…