4-Amino-4'-cyanobiphenyl → 4'-{[5-(3-Cyano-benzyloxy)-4,6-dimethyl-pyridin-3-ylmethyl]-amino}-biphenyl-4-carbonitrile

HRID 1158940Notes

Reaction equation

HRID 1158940 reaction equation
[CH:1]([C:3]1[C:4]([CH3:20])=[C:5]([O:10][CH2:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[C:6]([CH3:9])=[N:7][CH:8]=1)=O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1>>[C:15]([C:14]1[CH:13]=[C:12]([CH:19]=[CH:18][CH:17]=1)[CH2:11][O:10][C:5]1[C:4]([CH3:20])=[C:3]([CH2:1][NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)[CH:8]=[N:7][C:6]=1[CH3:9])#[N:16]

Participants

3

Reactant 2

HCID 971934-Amino-4'-cyanobiphenylHCID 586367933-(5-Formyl-2,4-dimethyl-pyridin-3-yloxymethyl)-benzonitrile

Product 1

HCID 586368394'-{[5-(3-Cyano-benzyloxy)-4,6-dimethyl-pyridin-3-ylmethyl]-amino}-biphenyl-4-carbonitrileYield 30%

Procedure

The reductive amination of 3-(5-formyl-2,4-dimethyl-pyridin-3-yloxymethyl)-benzonitrile (27) (10.0 g, 37.6 mmol) and 4-amino-4′-cyanobiphenyl (8.8 g, 45.1 mmol), as described in Example 21, gave 4′-{[5-(3-cyano-benzyloxy)-4,6-dimethyl-pyridin-3-ylmethyl]-amino}-biphenyl-4-carbonitrile (28) (5.0 g, 30% yield) as a colorless solid.

Sources & evidence

ORD record
ord-03c83b2e431448e399efa6a2a75c9392
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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