1,1'-Carbonyldiimidazole → 2-(4-(4,9-diethoxy-1-oxo-1H-benzo[f]isoindol-2(3H)-yl)phenyl)-N-((4-fluorophenyl)sulfonyl)acetamide

HRID 346711

반응식

HRID 346711 반응식
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:15][C:16]1[C:24]2[CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][CH:26]=3)[C:21](=[O:35])[C:20]=2[C:19]([O:36][CH2:37][CH3:38])=[C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=12)[CH3:14].[F:43][C:44]1[CH:49]=[CH:48][C:47]([S:50]([NH2:53])(=[O:52])=[O:51])=[CH:46][CH:45]=1.C(N(CC)C(C)C)(C)C>ClCCl>[CH2:13]([O:15][C:16]1[C:24]2[CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C:32]([NH:53][S:50]([C:47]4[CH:46]=[CH:45][C:44]([F:43])=[CH:49][CH:48]=4)(=[O:52])=[O:51])=[O:33])=[CH:27][CH:26]=3)[C:21](=[O:35])[C:20]=2[C:19]([O:36][CH2:37][CH3:38])=[C:18]2[CH:39]=[CH:40][CH:41]=[CH:42][C:17]=12)[CH3:14]

참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 1202314-FluorobenzenesulfonamideHCID 9931112[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid

생성물 1

HCID 98940822-(4-(4,9-diethoxy-1-oxo-1H-benzo[f]isoindol-2(3H)-yl)phenyl)-N-((4-fluorophenyl)sulfonyl)acetamide수율 35.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of carbonyldiimidazole (13.2 mg, 0.081 mmol) and [4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid (30 mg, 0.074 mmol) in dichloromethane (2 ml) was added 4-fluorobenzenesulphonamide (14.3 mg, 0.081 mmol) and N,N-diisopropylethylamine (10.5 mg, 0.81 mmol). The mixture was stirred at ambient temperature under an atmosphere of nitrogen overnight. The reaction mixture was diluted with dichloromethane (3 ml) and then washed with 2N hydrochloric acid (5 ml). The organic phase was dried (MgSO4) and then concentrated in vacuo to give a brown gum. The residue was purified using mass directed autopurification to give the title compound as a white solid (14.7 mg, 35.3%). MH+563.

후처리

  1. washwashed with 2N hydrochloric acid (5 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give a brown gum
  5. customThe residue was purified

출처 및 근거

ORD 기록
ord-74fcd33b573a41169ca8bf9fead8c9a7
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173047B2

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