HCID 68816757, compound → HCID 57845756, compound

HRID 735184Notes

Reaction equation

HRID 735184 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:33])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH3:32])[CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>[Ni].CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:33])[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH3:32])[CH:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68816757HCID 68816757, compound

Product 1

HCID 57845756HCID 57845756, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

A reaction mixture of 60 mg (0.13 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-{[methyl-(tetrahydropyran-4-yl)amino]methyl}phenyl)acrylamide and 20 mg of Raney nickel in 10 mL of DMF is hydrogenated for 3 hours at 50 psi and ambient temperature. The catalyst is filtered off and the filtrate is evaporated to dryness. The purification is carried out by column chromatography on silica gel (eluant: dichloromethane/methanol/ammonia (20:1:0.1)). Yield: 22 mg (29% of theory); melting point: 167° C.-173° C.; C28H31ClN2O2 (M=463.01); calc.: molecular ion peak (M+H)+: 463/65 (Cl); found: molecular ion peak (M+H)+: 463/65 (Cl).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated to dryness
  3. customThe purification

Sources & evidence

ORD record
ord-dc54610e57cb4adf9614eae26f974e6a
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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