3-Methoxycarbonyloxymethyl-aniline → HCID 57033237, compound
Reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH:9][C:10]=1[CH2:11][CH2:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2)=[O:5])C.[CH3:29][O:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38])=[O:32]>>[CH3:29][O:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[C:37]([NH:38][C:4]([C:6]2[N:7]=[C:8]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:9][C:10]=2[CH2:11][CH2:12][C:13]23[CH2:14][CH:15]4[CH2:21][CH:19]([CH2:18][CH:17]([CH2:16]4)[CH2:22]2)[CH2:20]3)=[O:5])[CH:39]=[CH:40][CH:41]=1)=[O:32]Participants
Procedure
5-(2-Adamantan-1-yl-ethyl)-2-phenyl-1H-imidazole4-carboxylic acid ethyl ester (Example 46) was hydrolized according to the procedure of Example 20, step c. The acid was reacted with 3-methoxycarbonyloxymethyl-aniline using the procedure of Example 20, step d to produce 5-(2-adamantan-1-yl-ethyl)-2-phenyl-1H-imidazole-4-carboxylic acid (3-methoxycarbonyloxymethyl-phenyl)-amide, which was deprotected according to the procedure of Example 22, step b to afford the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO) 12.69 (1H, br s), 9.56 (1H, s), 8.08 (2H, d), 7.80 (1H, s), 7.65 (1H, d), 7.48 (2H, t), 7.39 (1H, t), 7.26 (1H, t), 7.00 (1H, d), 5.16 (1H, m), 4.49 (2H, d), 2.99 (2H, m), 1.96 (3H, br s), 1.67-1.55 (12H, m), 1.43 (2H, m). Found: C, 76.26; H, 7.38; N, 9.09%; C29H33N3O2 requires: C, 76.45; H, 7.30; N, 9.22%.
Sources & evidence
- ORD record
- ord-261ee63796e04ea59e546f47edb32118
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
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