N-{2-[5-(4-chloro-2-nitrophenyl)-1,3,4-thiadiazole-2-sulfonylamino]-ethyl}-glycine ethyl ester → N-{2-[5-(4-Chloro-2-nitrophenyl)-1,3,4-thiadiazole-2-sulfonylamino]-ethyl}-N-{[6-N-(piperonyloxycarbonyl)-adenin-9-yl]-acetyl}-glycine Ethyl Ester
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].[CH2:29]([O:39][C:40]([NH:42][C:43]1[N:51]=[CH:50][N:49]=[C:48]2[C:44]=1[N:45]=[CH:46][N:47]2[CH2:52][C:53](O)=[O:54])=[O:41])[C:30]1[CH:38]=[CH:37][C:36]2[O:35][CH2:34][O:33][C:32]=2[CH:31]=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:53](=[O:54])[CH2:52][N:47]1[CH:46]=[N:45][C:44]2[C:48]1=[N:49][CH:50]=[N:51][C:43]=2[NH:42][C:40]([O:39][CH2:29][C:30]1[CH:38]=[CH:37][C:36]2[O:35][CH2:34][O:33][C:32]=2[CH:31]=1)=[O:41])[CH3:2]Participants
Reactant 2
Product 1
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-(piperonyloxycarbonyl)-adenin-9-yl]-acetic acid as per the procedure of example 13. 1H NMR (500 MHz; DMSO-d6) δ 10.60 (s, 0.45H), 10.59 (s, 0.55H), 9.31 (brs, 0.55H), 9.11 (brs, 0.45H), 8.58 (s, 0.45H), 8.57 (s, 0.55H), 8.40 (d, 0.55H), 8.39 (d, 0.45H), 8.32 (s, 0.55H), 8.31 (s, 0.45H), 8.03–7.98 (m, 1H), 7.93 (d, 0.55H), 7.90 (d, 0.45H), 7.05 (s, 1H), 6.95 (d, 1H), 6.91 (d, 1H), 6.02 (s, 2H), 5.38 (s, 1.1H), 5.17 (s, 0.9H), 5.11 (s, 2H), 4.48 (s, 0.9H), 4.23 (q, 0.9H), 4.08 (s, 1.1H), 4.07 (q, 1.1H), 3.73 (t, 1.1H), 3.54 (t, 1.1H), 3.45 (t, 0.9H), 3.30 (t, 0.9H), 1.27 (t, 1.35H), 1.15 (t, 1.65H).
Sources & evidence
- ORD record
- ord-709161fecf6448c7993ad3f83ddc96c0
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211668B2
Reaction notes
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