4-Amino-4'-cyanobiphenyl → 6-({3-Benzyloxy-5-[(4'-cyano-biphenyl-4-ylamino)-methyl]-2-methyl-pyridin-4-ylmethyl}-tert-butoxycarbonyl-amino)-hexanoic acid benzyl ester

HRID 1158949Notes

Reaction equation

HRID 1158949 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:23][C:24]1[C:29]([CH:30]=O)=[CH:28][N:27]=[C:26]([CH3:32])[C:25]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([C:55]#[N:56])=[CH:51][CH:50]=2)=[CH:45][CH:44]=1>>[CH2:1]([O:8][C:9](=[O:41])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:23][C:24]1[C:29]([CH2:30][NH:42][C:43]2[CH:44]=[CH:45][C:46]([C:49]3[CH:54]=[CH:53][C:52]([C:55]#[N:56])=[CH:51][CH:50]=3)=[CH:47][CH:48]=2)=[CH:28][N:27]=[C:26]([CH3:32])[C:25]=1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 971934-Amino-4'-cyanobiphenylHCID 586367916-[(3-Benzyloxy-5-formyl-2-methyl-pyridin-4-ylmethyl)-tert-butoxycarbonyl-amino]-hexanoic acid benzyl ester

Product 1

HCID 586367156-({3-Benzyloxy-5-[(4'-cyano-biphenyl-4-ylamino)-methyl]-2-methyl-pyridin-4-ylmethyl}-tert-butoxycarbonyl-amino)-hexanoic acid benzyl esterYield 83.3%

Procedure

The reductive amination of 6-[(3-benzyloxy-5-formyl-2-methyl-pyridin-4-ylmethyl)-tert-butoxycarbonyl-amino]-hexanoic acid benzyl ester (2.2 g, 3.9 mmol) and 4-amino-4′-cyanobiphenyl (2.1 g, 10.8 mmol), as described in Example 21, gave 6-({3-benzyloxy-5-[(4′-cyano-biphenyl-4-ylamino)-methyl]-2-methyl-pyridin-4-ylmethyl}-tert-butoxycarbonyl-amino)-hexanoic acid benzyl ester (44) (2.4 g, 83% yield).

Sources & evidence

ORD record
ord-b2440f1bf1cf4ce1998f144d8ec4f4c5
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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