Cesium carbonate → (4-Benzenesulfonyl-piperazin-1-yl)-[1-isopropyl-5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

HRID 1992474

반응식

HRID 1992474 반응식
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[NH:19][C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([C:27]([N:29]3[CH2:34][CH2:33][N:32]([CH:35]([CH3:37])[CH3:36])[CH2:31][CH2:30]3)=[O:28])=[CH:22][CH:21]=4)=[O:17])[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH:49]([CH3:51])[CH3:50])(=O)=O.C(=O)(O)[O-].[Na+]>C(#N)C>[C:1]1([S:7]([N:10]2[CH2:11][CH2:12][N:13]([C:16]([C:18]3[N:19]([CH:49]([CH3:51])[CH3:50])[C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([C:27]([N:29]3[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[CH2:33][CH2:34]3)=[O:28])=[CH:22][CH:21]=4)=[O:17])[CH2:14][CH2:15]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 13551Isopropyl methanesulfonateHCID 516892Sodium BicarbonateHCID 68535846(4-Benzenesulfonyl-piperazin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone

생성물 1

HCID 68536609(4-Benzenesulfonyl-piperazin-1-yl)-[1-isopropyl-5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone수율 39%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A suspension of 0.20 g (0.38 mmol) (4-benzenesulfonyl-piperazin-1-yl)-[5-(4-isopropyl-piperazine-1-carbonyl)-1H-indol-2-yl]-methanone (example 13), 0.25 g (0.77 mmol) caesium carbonate and isopropyl methanesulfonate in 4 mL acetonitrile was heated 16 h under reflux. After cooling to room temperature, the mixture was poured into saturated aqueous sodium bicarbonate solution and the phases were separated. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel with dichloromethane:methanol (19:1 v/v) as eluant to afford 0.85 g (39%) of the desired compound as a light brown foam. MS (ISP): 566.4 (M+H)+.

후처리

  1. temperaturewas heated 16 h
  2. temperatureunder reflux
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography on silica gel with dichloromethane:methanol (19:1 v/v) as eluant

출처 및 근거

ORD 기록
ord-4d7750247d5b4b7ea20b23d2787e9dd9
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07648979B2

연결된 노트

불러오는 중…