Cesium carbonate → tert-Butyl(S)-1-(4-chlorophenyl)-4-(4-(isoquinolin-6-yl)-1H-pyrazol-1-yl)butan-2-ylcarbamate

HRID 598896

반응식

HRID 598896 반응식
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[CH:12]=[N:11][CH:10]=[CH:9]3)[CH:3]=[N:2]1.CS(O[CH2:21][CH2:22][C@@H:23]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C([O-])(O)=O.[Na+]>[Cl:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][C@H:23]([NH:32][C:33](=[O:34])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:22][CH2:21][N:1]2[CH:5]=[C:4]([C:6]3[CH:7]=[C:8]4[C:13](=[CH:14][CH:15]=3)[CH:12]=[N:11][CH:10]=[CH:9]4)[CH:3]=[N:2]2)=[CH:30][CH:29]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 57950570(S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonateHCID 579506126-(1H-pyrazol-4-yl)isoquinoline

생성물 1

HCID 86635700tert-Butyl(S)-1-(4-chlorophenyl)-4-(4-(isoquinolin-6-yl)-1H-pyrazol-1-yl)butan-2-ylcarbamate수율 101.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

A mixture of 6-(1H-pyrazol-4-yl)isoquinoline (130 mg, 0.67 mmol), (S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butyl methanesulfonate (327 mg, 0.87 mmol) (prepared as shown in Scheme 15), and cesium carbonate (434 mg, 1.33 mmol) in DMF (5 mL) was stirred at room temperature for 24 hours. The mixture was diluted with saturated aqueous NaHCO3 and extracted with DCM (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (acetone/hexanes=0-40%) to provide the product as a tan solid (324 mg, 100%). LCMS (API-ES) m/z: 477 (M+H+).

후처리

  1. extractionextracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified

출처 및 근거

ORD 기록
ord-71a33c3e008b4353a56d03f48158d2de
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

연결된 노트

불러오는 중…