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

反応式

HRID 13276 の反応式
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]

参加物

8

反応物 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、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c8231d564b8f4c74832616ebad262bfa
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

関連ノート

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