Benzoic acid, 3-amino-, methyl ester → HCID 18405696, compound
Reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[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.C[O:32][C:33](=[O:41])[C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([NH2:40])[CH:35]=1>>[C:13]12([CH2:12][CH2:11][C:10]3[NH:9][C:8]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([Cl:30])[CH:24]=4)=[N:7][C:6]=3[C:4]([NH:40][C:36]3[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=3)[C:33]([OH:41])=[O:32])=[O:5])[CH2:22][CH:17]3[CH2:16][CH:15]([CH2:21][CH:19]([CH2:18]3)[CH2:20]1)[CH2:14]2Participants
Procedure
5-Adamantan-1-yl-2,3-dioxo-pentanoic acid ethyl ester monohydrate (Example 44) was reacted with 3,4-dichlorobenzaldehyde according to the procedure of Example 20, step b to produce 5-(2-adamantan-1-yl-ethyl)-2-(3,4-dichloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester. The ester was hydrolyzed according to the procedure of Example 20, step c and the resulting 5-(2-adamantan-1-yl-ethyl)-2-(3,4-dichloro-phenyl)-1-H-imidazole-4-carboxylic acid was reacted with 3-amino-benzoic acid methyl ester using essentially the same procedure as in Example 52, step a. Deprotection was carried out following essentially the procedure of Example 36, step d to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.89 (2H, br s), 9.90 (1H, s), 8.50 (1H, s), 8.32 (1H, s), 8.03 (2H, m), 7.76 (1H, d), 7.63 (1H, d), 7.43 (1H, t), 2.98 (2H, m), 1.97 (3H, s), 1.70-1.39 (14H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 56.90; H, 6.44; N, 7.08%; C36H46Cl2N4O8.1.6 H2O requires: C, 56.72; H, 6.50; N, 7.35%.
Sources & evidence
- ORD record
- ord-6a69af36f6004c959e6ce139b299e899
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
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