3,5-Difluorophenylacetic acid → 3-(4-[2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoylamino]-imidazol-1-yl)-3-methyl-butyric acid methyl ester

HRID 1714295Notes

Reaction equation

HRID 1714295 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]([N:8]1[CH:12]=[C:11]([NH:13][C:14](=[O:20])[CH:15]([NH2:19])[CH2:16][CH2:17][CH3:18])[N:10]=[CH:9]1)([CH3:7])[CH3:6].[F:22][C:23]1[CH:24]=[C:25]([CH2:30][C:31](O)=[O:32])[CH:26]=[C:27]([F:29])[CH:28]=1>>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]([N:8]1[CH:12]=[C:11]([NH:13][C:14](=[O:20])[CH:15]([NH:19][C:31](=[O:32])[CH2:30][C:25]2[CH:24]=[C:23]([F:22])[CH:28]=[C:27]([F:29])[CH:26]=2)[CH2:16][CH2:17][CH3:18])[N:10]=[CH:9]1)([CH3:6])[CH3:7]

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 671653603-[4-(2-Amino-pentanoylamino)-imidazol-1-yl]-3-methyl-butyric acid methyl ester

Product 1

HCID 116121213-(4-[2-[2-(3,5-Difluoro-phenyl)-acetylamino]-pentanoylamino]-imidazol-1-yl)-3-methyl-butyric acid methyl ester

Procedure

3-[4-(2-Amino-pentanoylamino)-imidazol-1-yl]-3-methyl-butyric acid methyl ester was coupled with (3,5-Difluoro-phenyl)-acetic acid to provide the title compound: C13 NMR (100 MHz, CDCl3) 13.9, 19.0, 27.9, 28.1, 35.9, 42.7, 46.8, 51.8, 53.1, 56.3, 102.2, 102.5, 102.7, 105.1, 112.2, 112.3, 112.4, 112.5, 131.3, 137.9, 139.2, 161.8, 164.2, 164.3, 169.4, 169.9, 170.0; MS 451.2 m/z (M+1).

Sources & evidence

ORD record
ord-a14efb0eea614b349c13d1d092991756
Source dataset
uspto-grants-2010_09
Patent number
US07795447B2

Reaction notes

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