5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid → 5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid (3-benzenesulfonylaminocarbonyl-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]([CH:44]=[CH:45][CH:46]=1)[C:32]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])=[O:33]>>[C:38]1([S:35]([NH:34][C:32]([C:31]2[CH:30]=[C:29]([NH:28][C:25]([C:14]3[N:15]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH3:24])[NH:17][C:13]=3[CH2:12][CH2:11][C:1]34[CH2:10][CH:5]5[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]5)[CH2:8]3)[CH2:2]4)=[O:26])[CH:46]=[CH:45][CH:44]=2)=[O:33])(=[O:37])=[O:36])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1Participants
3
Procedure
5-(2-Adamantan-1-yl-ethyl)-2-o-tolyl-1H-imidazole-4-carboxylic acid (Example 93) was reacted with N-(3-amino-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), 9.70 (1H, br s), 8.29 (1H, s), 7.98 (3H, m), 7.68-7.52 (SH, m), 7.42-7.28 (4H, m), 2.98 (2H, m), 2.54 (3H, s), 1.95 (3H, s), 1.67-1.35 (14H, m). Found: C, 67.65; H, 6.34; N, 8.49%; 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-ec34a76034004ca5820140916e740f3b
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
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