2-(4-(((Benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid → 4-{[4-N-(Benzhydryloxycarbonyl)-cytosin-1-yl]acetyl}-1-(4-chloro-2-nitro-benzenesulfonyl)-piperazin-2-one

HRID 1794959Notes

Reaction equation

HRID 1794959 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C:13]2=[O:18])(=[O:11])=[O:10])=[C:5]([N+:19]([O-:21])=[O:20])[CH:4]=1.[CH:22]([O:35][C:36]([NH:38][C:39]1[CH:44]=[CH:43][N:42]([CH2:45][C:46](O)=[O:47])[C:41](=[O:49])[N:40]=1)=[O:37])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH:22]([O:35][C:36]([NH:38][C:39]1[CH:44]=[CH:43][N:42]([CH2:45][C:46]([N:15]2[CH2:16][CH2:17][N:12]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][C:5]=3[N+:19]([O-:21])=[O:20])(=[O:11])=[O:10])[C:13](=[O:18])[CH2:14]2)=[O:47])[C:41](=[O:49])[N:40]=1)=[O:37])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 155130422-(4-(((Benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acidHCID 688009591-(4-chloro-2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt

Product 1

HCID 222223654-{[4-N-(Benzhydryloxycarbonyl)-cytosin-1-yl]acetyl}-1-(4-chloro-2-nitro-benzenesulfonyl)-piperazin-2-oneYield 27.4%

Procedure

The title compound (0.56 g, 27%) was synthesized by reaction of 1-(4-chloro-2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt (1.07 g, 3.0 mmol) with [4-N-(benzhydryloxycarbonyl)-cytosin-1-yl]-acetic acid (1.14 g, 3.0 mmol), as per the procedure of example 77. 1H NMR(DMSO-d6) δ 10.98(s, 11H), 8.40(s, 1H), 8.32(m, 11H), 8.07(m, 11H), 7.89(d, 0.6H), 7.85(d, 0.4H), 7.46˜7.28(m, 1H), 6.96(m, 1H), 6.79(s, 1H), 4.81(s, 1.2H), 4.73(s, 0.8H), 4.45(s, 0.8H), 4.27(s, 1.2H), 4.07˜3.97(m, 2.4H), 3.90˜3.80(m, 1.6H).

Sources & evidence

ORD record
ord-92d1db5979e24fa5a4900424ec3ddc93
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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