[4-N-(2-methylthioethoxycarbonyl)-cytosin-1-yl]-acetic acid → 1-(Benzothiazole-2-sulfonyl)-4-{[4-N-(2-methylthioethoxycarbonyl)-cytosin-1-yl]-acetyl}-piperazin-2-one
Reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C:21]1=[O:26])(=[O:19])=[O:18].[CH3:27][S:28][CH2:29][CH2:30][O:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][N:38]([CH2:41][C:42](O)=[O:43])[C:37](=[O:45])[N:36]=1)=[O:33]>>[S:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17]([N:20]1[CH2:25][CH2:24][N:23]([C:42](=[O:43])[CH2:41][N:38]2[CH:39]=[CH:40][C:35]([NH:34][C:32]([O:31][CH2:30][CH2:29][S:28][CH3:27])=[O:33])=[N:36][C:37]2=[O:45])[CH2:22][C:21]1=[O:26])(=[O:19])=[O:18]Participants
3
Procedure
The title compound was synthesized by the reaction of 1-(benzothiazole-2-sulfonyl)-piperazin-2-one trifluoroacetic acid salt with [4-N-(2-methylthioethoxycarbonyl)-cytosin-1-yl]-acetic acid as per the procedure of Example 52. 1H NMR (500 MHz; DMSO-d6) δ 10.72 (brs, 1H), 8.34 (m, 1H), 8.26 (m, 1H), 7.90 (d, 0.6H), 7.84 (d, 0.4H), 7.72 (m, 2H), 7.01 (t, 1H), 4.82 (s, 1.2H), 4.71 (s, 0.8H), 4.45 (s, 0.8H), 4.27 (s, 1.2H), 4.26 (t, 2H), 4.22 (t, 1.2H), 4.07 (t, 0.8H), 3.99 (t, 1.2H), 3.86 (t, 0.8H), 2.73 (t, 2H), 2.11 (s, 3H).
Sources & evidence
- ORD record
- ord-6defbc0328234a1b91d2fa931cda7712
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371859B2
Reaction notes
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