Ethanol → 1-(2-(6-(4-fluoro-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-piperidin-1-yl)-ethanone

HRID 13289

Reaktionsgleichung

Reaktionsgleichung von HRID 13289
C(O)C.[NH2:4][C:5]1[C:6]([N+:28]([O-])=O)=[CH:7][C:8]([O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2[C:17](=[O:19])[CH3:18])[CH:10]=1.[H][H].[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH:39]=O>[Ni].CN1CCCC1=O.O>[F:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:8]2[C:9]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][N:12]3[C:17](=[O:19])[CH3:18])=[CH:10][C:5]3[NH:4][C:39]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=4)=[N:28][C:6]=3[CH:7]=2)=[CH:22][CH:23]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 142732-PyridinecarboxaldehydeHCID 231454081-(2-(5-Amino-2-(4-fluoro-phenoxy)-4-nitro-phenyl)-piperidin-1-yl)-ethanoneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 231452871-(2-(6-(4-fluoro-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-piperidin-1-yl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

50 mg of developed Raney nickel catalyst was added to an ethanol (10 ml) solution of 180 mg of 1-(2-(5-amino-2-(4-fluoro-phenoxy)-4-nitro-phenyl)-piperidin-1-yl)-ethanone, and the reaction liquid was stirred overnight in a hydrogen atmosphere. The catalyst was removed through filtration through Celite, and the filtrate was distilled under reduced pressure to obtain 171 mg of a crude product. 50 mg of the resulting crude product was dissolved in 1 ml of N-methylpyrrolidone, and 16 mg of pyridine-2-carboxaldehyde was added to it, and the reaction liquid was stirred at room temperature for 3 days. Water was added to the reaction liquid, and extracted with ethyl acetate, and 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 reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid] to obtain the entitled compound as a pale yellow solid.

Aufarbeitung

  1. customthe reaction liquid
  2. customThe catalyst was removed through filtration through Celite
  3. distillationthe filtrate was distilled under reduced pressure
  4. customto obtain 171 mg of 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 reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]

Quellen und Nachweise

ORD-Eintrag
ord-5e20a6940d494e8fb0745a7a91b65f9f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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