HCID 18405518, compound → HCID 18405676, compound

HRID 1018360Notes

Reaction equation

[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[C:24](O)=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([O:29][C:30]([C:32]1([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([NH2:43])[CH:38]=2)[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31])C>>[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)=[N:15][C:14]=3[C:24]([NH:43][C:39]3[CH:38]=[C:37]([C:32]4([C:30]([OH:29])=[O:31])[CH2:33][CH2:34][CH2:35][CH2:36]4)[CH:42]=[CH:41][CH:40]=3)=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

Reactant 2

HCID 18405518HCID 18405518, compound

HCID 53948864HCID 53948864, compound

Product 1

HCID 18405676HCID 18405676, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) was reacted with 1-(3-amino-phenyl)-1-cyclopentanecarboxylic acid ethyl ester (prepared from 1-(4-chloro-phenyl)-1-cyclopentanecarboxylic acid using Mutti's procedure (S. Mutti et al. Synth. Comm. 1997, 27, 425)) according to the procedure of Example 20, step d. The ethyl ester was hydrolysed using the same procedure as in Example 247, step b to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.00 (1H, br s), 9.29 (1H, br s), 7.63 (2H, m), 7.16 (1H, m), 7.02 (1H, d), 2.85 (2H, m), 2.49 (3H, m), 1.98-1.34 (33H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 62.88; H, 8.79; N, 7.07%. C41H62N4O8.2.5 mols H2O requires: C, 62.81; H, 8.61; N, 7.15%.

Sources & evidence

ORD record: ord-74138cf70a1046179149781f6aca1317
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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