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

HRID 1748688노트

반응식

HRID 1748688 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-193394df043047bcb842cd98228ef49b
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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