Cesium carbonate → 6-[2-(4-Cyano-phenyl)-2H-pyrazol-3-yl]-5-methyl-3-oxo-4-(3-trifluoromethyl-phenyl)-3,4-dihydro-pyrazine-2-carboxylic acid methylamide

HRID 1640682노트

반응식

HRID 1640682 반응식
Br[C:2]1[N:7]=[C:6]([C:8]([NH:10][CH3:11])=[O:9])[C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:3]=1[CH3:23].[C:24]([C:26]1[CH:31]=[CH:30][C:29]([N:32]2[C:36](B(O)O)=[CH:35][CH:34]=[N:33]2)=[CH:28][CH:27]=1)#[N:25].C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC>[CH3:11][NH:10][C:8]([C:6]1[C:5](=[O:12])[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:3]([CH3:23])=[C:2]([C:36]2[N:32]([C:29]3[CH:30]=[CH:31][C:26]([C:24]#[N:25])=[CH:27][CH:28]=3)[N:33]=[CH:34][CH:35]=2)[N:7]=1)=[O:9]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 667386596-Bromo-N,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamideHCID 66738661[1-(4-cyanophenyl)-1H-pyrazol-5-yl]boronic acid

생성물 1

HCID 248901406-[2-(4-Cyano-phenyl)-2H-pyrazol-3-yl]-5-methyl-3-oxo-4-(3-trifluoromethyl-phenyl)-3,4-dihydro-pyrazine-2-carboxylic acid methylamide수율 20%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
110 °C

실험 절차

6-Bromo-N,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide (SM2, 0.05 g, 0.128 mmol), 1-(4-cyanophenyl)-1H-pyrazol-5-boronic acid (SM4, 0.062 g, 0.256 mmol), Cs2CO3 (0.125 g, 0.384 mmol) and DME (3 ml) were added to a glass tube for microwave synthesis. The mixture was degassed with nitrogen and Pd(PBut3)2 (0.010 g) was added. The tube was sealed and heated with stirring at 110° C. (150 W) in a microwave heater for 10 minutes. The mixture was diluted with EtOAc (5 ml), and filtered. The solution was concentrated in vacuo and was purified by chromatography on silica to give a reasonably pure material that was further purified by preparative HPLC to give 0.012 g (20%) of the title compound as a white solid.

후처리

  1. customThe mixture was degassed with nitrogen and Pd(PBut3)2 (0.010 g)
  2. additionwas added
  3. customThe tube was sealed
  4. temperatureheated
  5. additionThe mixture was diluted with EtOAc (5 ml)
  6. filtrationfiltered
  7. concentrationThe solution was concentrated in vacuo
  8. customwas purified by chromatography on silica
  9. customto give a reasonably pure material that
  10. customwas further purified by preparative HPLC

출처 및 근거

ORD 기록
ord-954f1f8700f24b98a5237693465b3ed5
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114881B2

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