4-Aminobenzonitrile → HCID 68644511, compound

HRID 1158952Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:17][C:18]1[C:23]([CH:24]=O)=[CH:22][N:21]=[C:20]([CH3:26])[C:19]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:37][C:38]1[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=1>>[C:1]([O:5][C:6]([N:8]([CH2:17][C:18]1[C:23]([CH2:24][NH:37][C:38]2[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=2)=[CH:22][N:21]=[C:20]([CH3:26])[C:19]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 86604776HCID 86604776, compound

Product 1

HCID 68644511HCID 68644511, compoundYield 752.9%

Procedure

The reductive amination of 6-{tert-butoxycarbonyl-[3-(4-cyano-benzyloxy)-5-formyl-2-methyl-pyridin-4-ylmethyl]-amino}-hexanoic acid (52) (0.9 g, 0.2 mmol) and 4-aminobenzonitrile (1.6 g, 13.5 mmol), as described in Example 21, gave 6-(tert-butoxycarbonyl-{3-(4-cyano-benzyloxy)-5-[(4-cyano-phenylamino)-methyl]-2-methyl-pyridin-4-ylmethyl}-amino)-hexanoic acid (53) (0.9 g, 81% yield).

Sources & evidence

ORD record: ord-5a911b242e26412f841be514ccdf3155
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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