Dimethylformamide → 4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamide

HRID 872989노트

반응식

HRID 872989 반응식
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[C:13](=[O:25])[N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:15]([CH3:18])[C:16]=1[CH3:17])=[O:11].CC([O-])(C)C.[K+].CN(C=O)C.Cl[C:38]1[CH:43]=[CH:42][N:41]=[C:40]([C:44]([NH2:46])=[O:45])[CH:39]=1>CCOC(C)=O.O>[CH3:18][N:15]1[C:16]([CH3:17])=[C:12]([C:10]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([O:8][C:38]3[CH:43]=[CH:42][N:41]=[C:40]([C:44]([NH2:46])=[O:45])[CH:39]=3)=[CH:7][C:2]=2[F:1])=[O:11])[C:13](=[O:25])[N:14]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 3035434-Chloropyridine-2-carboxamideHCID 23665647Potassium tert-butoxideHCID 90032748N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

생성물 1

HCID 730510744-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-3-fluorophenoxy)picolinamide수율 91.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of N-(2-fluoro-4-hydroxyphenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (300 mg, 0.879 mmol) and t-BuOK (118 mg, 1.05 mmol) was added DMF (2.5 mL). The resulted mixture was stirred at rt for 30 minutes, then 4-chloropicolinamide (165 mg, 1.05 mmol) was added. The mixture was heated at 120° C. for 5 hours, then cooled to rt, and H2O (50 mL) and EtOAc (2 mL) was added. The resulted mixture was stirred at rt overnight. Filtered and the precipitation was washed with water (5 mL) to give the title compound as a dark brown solid (370 mg, 91.2%).

후처리

  1. temperatureThe mixture was heated at 120° C. for 5 hours
  2. temperaturecooled to rt
  3. stirringThe resulted mixture was stirred at rt overnight
  4. filtrationFiltered
  5. customthe precipitation
  6. washwas washed with water (5 mL)

출처 및 근거

ORD 기록
ord-3a7428f05d894e0ca65b852acbb2dd0e
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975282B2

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