HCID 11271708, compound → HCID 59853755, compound

HRID 2374286Notes

Reaction equation

HRID 2374286 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][C:8]=2[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23](=O)[CH3:24])=[CH:19][C:18]=3[F:26])[CH2:13][CH2:12]2)=[O:10])[CH2:3][CH2:2]1>CCO.[Ni]>[CH2:23]([C:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:9]([C:8]3[CH:27]=[C:28]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:29]=[CH:30][C:7]=3[CH:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[O:10])[CH2:12][CH2:13]2)=[C:18]([F:26])[CH:19]=1)[CH3:24]

Participants

4

Reactant 1

HCID 11271708HCID 11271708, compound

Product 1

HCID 59853755HCID 59853755, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

1-(4-{4-[2-(3,6-Dihydro-2H-pyran-4-yl)-5-methanesulfonyl-benzoyl]-piperazin-1-yl}-3-fluoro-phenyl)-ethanone (Example 72) is hydrogenated in EtOH in presence of Raney nickel under a hydrogen pressure of 100 bar at 100IC for 18 h. Filtration, evaporation of the solvent and purification of the residue by preparative HPLC on a C-18 column with a H2O/MeCN gradient provided [4-(4-Ethyl-2-fluoro-phenyl)-piperazin-1-yl]-[5-methanesulfonyl-2-(tetrahydro-pyran-4-yl)-phenyl]-methanone in 41% yield as colourless crystals (M+H+: 475.5.).

Workup

  1. customfor 18 h
  2. filtrationFiltration, evaporation of the solvent and purification of the residue by preparative HPLC on a C-18 column with a H2O/MeCN gradient

Sources & evidence

ORD record
ord-88b039746c8048d2801f0e521d381074
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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