4-Aminobenzonitrile → HCID 86604777, compound

HRID 1158989Notes

Reaction equation

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

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 58636746HCID 58636746, compound

Product 1

HCID 86604777HCID 86604777, compoundYield 67.5%

Procedure

The reductive amination of 3-(5-formyl-2,4-dimethyl-6-propyl-pyridin-3-yloxymethyl)-benzonitrile (179) (675 mg, 2.18 mmol) and 4-aminobenzonitrile (516 mg, 4.4 mmol), was carried out as described in Example 21, gave 4-{[5-(3-cyano-benzyloxy)-4,6-dimethyl-2-propyl-pyridin-3-ylmethyl]-amino}-benzonitrile (180) (324 mg, 36% yield).

Sources & evidence

ORD record: ord-15a107f4d6534bd2be9ceb54d4946908
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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