3',4'-Dimethoxy-2-(2-propenyl)-N-[1-methyl-4-(3-pyridinyl)butyl][1,1'-biphenyl]-4-carb oxamide → (R)-3',4'-Dimethoxy-2-propyl-N-[1-methyl-4-(3-Pyridinyl)butyl][1,1'-biphenyl]-4-carboxamide

HRID 2073323Notes

Reaction equation

HRID 2073323 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH:19][CH:20]([CH3:30])[CH2:21][CH2:22][CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[O:18])=[CH:13][C:12]=2[CH2:31][CH:32]=[CH2:33])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH:19][C@H:20]([CH3:30])[CH2:21][CH2:22][CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[O:18])=[CH:13][C:12]=2[CH2:31][CH2:32][CH3:33])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 1

HCID 145701063',4'-Dimethoxy-2-(2-propenyl)-N-[1-methyl-4-(3-pyridinyl)butyl][1,1'-biphenyl]-4-carb oxamide

Product 1

HCID 14570109(R)-3',4'-Dimethoxy-2-propyl-N-[1-methyl-4-(3-Pyridinyl)butyl][1,1'-biphenyl]-4-carboxamideYield 94.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 282 mg of 3',4'-Dimethoxy-2-(2-propenyl)-N-[1-methyl-4-(3-pyridinyl)butyl][1,1'-biphenyl]-4-carb oxamide was hydrogenated over 40 mg of 10% palladium on carbon to give 268 mg of (R)-3',4'-Dimethoxy-2-propyl-N-[1-methyl-4-(3-Pyridinyl)butyl][1,1'-biphenyl]-4-carboxamide as a foam.

Sources & evidence

ORD record
ord-b22dbcb974ff4fa9ba40ce6c6da05aae
Source dataset
uspto-grants-1990_04
Patent number
US04916145

Reaction notes

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