N-{2-[5-(4-chloro-2-nitrophenyl)-1,3,4-thiadiazole-2-sulfonylamino]-ethyl}-glycine ethyl ester → HCID 21092788, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][NH:6][CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[N+:25]([O-:27])=[O:26])=[N:16][N:17]=1)(=[O:12])=[O:11])[CH3:2].[CH3:29][O:30][C:31]1[CH:54]=[CH:53][C:34]([CH2:35][O:36][C:37]([NH:39][C:40]2[N:48]=[CH:47][N:46]=[C:45]3[C:41]=2[N:42]=[CH:43][N:44]3[CH2:49][C:50](O)=[O:51])=[O:38])=[CH:33][CH:32]=1>>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:7][CH2:8][NH:9][S:10]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[N+:25]([O-:27])=[O:26])=[N:16][N:17]=1)(=[O:12])=[O:11])[C:50](=[O:51])[CH2:49][N:44]1[CH:43]=[N:42][C:41]2[C:45]1=[N:46][CH:47]=[N:48][C:40]=2[NH:39][C:37]([O:36][CH2:35][C:34]1[CH:53]=[CH:54][C:31]([O:30][CH3:29])=[CH:32][CH:33]=1)=[O:38])[CH3:2]Participants
Procedure
The title compound was synthesized by the reaction of N-{2-[5-(4-chloro-2-nitrophenyl)-1,3,4-thiadiazole-2-sulfonylamino]-ethyl}-glycine ethyl ester with [6-N-(4-methoxybenzyloxycarbonyl)-adenin-9-yl]-acetic acid as per the procedure of example 13. 1H NMR (500 MHz; DMSO-d6) δ 10.56 (s, 1H), 10.59 (s, 0.55H), 9.31 (brs, 0.55H), 9.11 (brs, 0.45H), 8.57 (s, 0.45H), 8.56 (s, 0.55H), 8.40 (d, 0.55H), 8.39 (d, 0.45H), 8.31 (s, 0.55H), 8.30 (s, 0.45H), 8.03–7.99 (m, 1H), 7.93 (d, 0.55H), 7.91 (d, 0.45H), 7.39 (d, 1H), 6.95 (d, 2H), 5.38 (s, 1.1H), 5.17 (s, 0.9H), 5.14 (s, 2H), 4.48 (s, 0.9H), 4.23 (q, 0.9H), 4.08 (s, 1.1H), 4.07 (q, 1.1H), 3.76 (s, 3H), 3.72 (t, 1.1H), 3.54 (t, 1.1H), 3.45 (t, 0.9H), 3.29 (t, 0.9H), 1.27 (t, 1.35H), 1.15 (t, 1.65H).
Sources & evidence
- ORD record
- ord-ed97510786e749d7a2d495136c8be82b
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211668B2
Reaction notes
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