Ethanol → 2,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13276

반응식

HRID 13276 반응식
C(O)C.[NH2:4][C:5]1[C:6]([N+:33]([O-])=O)=[CH:7][C:8]([O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH:10]=1.[H][H].[N:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[CH:44]=O>[Ni].O.CO>[F:18][C:17]([F:20])([F:19])[C:16]([N:12]1[CH2:13][CH2:14][CH2:15][CH:11]1[C:9]1[C:8]([O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:7][C:6]2[N:33]=[C:44]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][N:38]=3)[NH:4][C:5]=2[CH:10]=1)=[O:21]

참가 물질

8

반응물 4

HCID 702EthanolHCID 142732-PyridinecarboxaldehydeHCID 231451471-(2-(5-Amino-2-(4-methanesulfonyl-phenoxy)-4-nitro-phenyl)-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 231457212,2,2-trifluoro-1-(2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

시약·촉매·용매 3

HCID 935Nickel촉매HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

100 mg of developed Raney nickel catalyst was added to an ethanol (10 ml) solution of 521 mg of 1-(2-(5-amino-2-(4-methanesulfonyl-phenoxy)-4-nitro-phenyl)-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone, and the reaction liquid was stirred overnight in a hydrogen atmosphere. The catalyst was removed through filtration through Celite, and the solvent was evaporated away under reduced pressure to obtain a crude product. 226 mg of pyridine-2-carboxaldehyde was added to a methanol (10 ml) solution of 448 mg of the resulting crude product, and the reaction liquid was stirred overnight at 50° C. Water was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=20/1) to obtain the entitled compound as a pale yellow solid.

후처리

  1. customthe reaction liquid
  2. customThe catalyst was removed through filtration through Celite
  3. customthe solvent was evaporated away under reduced pressure
  4. customto obtain a crude product
  5. customthe reaction liquid
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated saline
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe solvent was evaporated away under reduced pressure
  10. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=20/1)

출처 및 근거

ORD 기록
ord-c8231d564b8f4c74832616ebad262bfa
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728025B2

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