3-amino-N-benzoyl-benzenesulfonamide → 5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic Acid (3-benzoylsulfamoyl-phenyl)-amide
Reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])=[N:15][C:14]=3[C:25](O)=[O:26])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:28][C:29]1[CH:30]=[C:31]([S:35]([NH:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>>[C:39]([NH:38][S:35]([C:31]1[CH:30]=[C:29]([NH:28][C:25]([C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH3:24])[NH:17][C:13]=2[CH2:12][CH2:11][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)=[O:26])[CH:34]=[CH:33][CH:32]=1)(=[O:37])=[O:36])(=[O:46])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1Participants
3
Procedure
5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid (Example 93) was reacted with 3-amino-N-benzoyl-benzenesulfonamide using essentially the same procedure as in Example 20, step d. The crude product was purified by flash column chromatography (silica, ethyl acetate/hexane 2:1) to afford the title compound. 1H NMR 300 MHz, d6-DMSO) 12.52 (1H, br s), 9.85 (1H, br s), 8.55 (1H, br s), 7.89 (3H, m), 7.62-7.29 (9H, m), 2.99 (2H, m), 2.54 (3H, s), 1.95 (3H, s), 1.66-1.40 (14H, m). Found: C, 67.51; H, 6.33; N, 8.63%; C36H38N4O4S.1.0 H2O requires: C, 67.48; H, 6.29; N, 8.74%.
Workup
- customThe crude product was purified by flash column chromatography (silica, ethyl acetate/hexane 2:1)
Sources & evidence
- ORD record
- ord-65363a399d594b3fac75b9cc60813ef9
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
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