4-Aminobenzonitrile → HCID 68644234, compound

HRID 1158965Notes

Reaction equation

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

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 68644138HCID 68644138, compound

Product 1

HCID 68644234HCID 68644234, compoundYield 45.1%

Procedure

The reductive amination of 4-(5-carboxy-2,4-dimethyl-pyridin-3-yloxy)-benzonitrile (189 mg, 0.75 mmol) and 4-aminobenzonitrile (400 mg, 3.38 mmol), as described in Example 21, gave 4-{[3-(4-cyano-phenoxy)-2,4-dimethyl-pyridin-5-ylmethyl]-amino}-benzonitrile (91) (120 mg, 45% yield) as a brown oil.

Sources & evidence

ORD record: ord-9d9dc42992154b65b6fb308126525979
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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