Carbon Dioxide → 1-{4-[4-(2-Chloro-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone

HRID 32660노트

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HRID 32660 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[F:30][C:31]1[CH:32]=[C:33]([C:43](=[O:45])[CH3:44])[CH:34]=[CH:35][C:36]=1[N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([N:40]1[CH2:39][CH2:38][N:37]([C:36]2[CH:35]=[CH:34][C:33]([C:43](=[O:45])[CH3:44])=[CH:32][C:31]=2[F:30])[CH2:42][CH2:41]1)=[O:6]

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 6856101-(3-Fluoro-4-piperazin-1-ylphenyl)ethanoneHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

생성물 1

HCID 597937161-{4-[4-(2-Chloro-5-methanesulfonyl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone수율 49.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a solution of 2-Chloro-5-methanesulfonyl-benzoic acid (200 mg, 0.852 mmol) in DMF (3 ml) was added dropwise 1,1′-Carbonyldiimidazole (142 mg, 0.852 mmol). When the CO2 evolution ceased, the mixture was heated to 50° C. for 15 minutes. The mixture was cooled to room temperature. 1-(3-Fluoro-4-piperazin-1-yl-phenyl)-ethanone (189 mg, 0.852 mmol) was added portionwise. The mixture was stirred at room temperature for 1 hour. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate. The solution was washed twice with water, dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was purified on silica gel (Heptane/AcOEt 0%-50% (15 minutes) to provide the title compound (185 mg, 49%) as a white solid, MS (m/e): 439.1 (M+H+, 100%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe solution was washed twice with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe crude oil was purified on silica gel (Heptane/AcOEt 0%-50% (15 minutes)

출처 및 근거

ORD 기록
ord-25180767455a444ebbeb70ba5d8cca36
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427612B2

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