1-(4-chloro-2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt → 4-{[2-N-(Benzyloxycarbonyl)-guanin-9-yl]acetyl}-1-(4-chloro-2-nitro-benzenesulfonyl)-piperazin-2-one

HRID 1794963Notes

Reaction equation

HRID 1794963 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.[CH2:22]([O:29][C:30]([NH:32][C:33]1[NH:34][C:35](=[O:46])[C:36]2[N:37]=[CH:38][N:39]([CH2:42][C:43](O)=[O:44])[C:40]=2[N:41]=1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([O:29][C:30]([NH:32][C:33]1[NH:34][C:35](=[O:46])[C:36]2[N:37]=[CH:38][N:39]([CH2:42][C:43]([N:15]3[CH2:16][CH2:17][N:12]([S:9]([C:6]4[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][C:5]=4[N+:19]([O-:21])=[O:20])(=[O:11])=[O:10])[C:13](=[O:18])[CH2:14]3)=[O:44])[C:40]=2[N:41]=1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 688009591-(4-chloro-2-nitro-benzenesulfonyl)-piperazin-2-one HCl saltHCID 1354406332-[2-(Benzyloxycarbonylamino)-6-hydroxy-purin-9-yl]acetic acid

Product 1

HCID 1363776454-{[2-N-(Benzyloxycarbonyl)-guanin-9-yl]acetyl}-1-(4-chloro-2-nitro-benzenesulfonyl)-piperazin-2-oneYield 60%

Procedure

The title compound (1.32 g, 60%) was synthesized by reaction of 1-(4-chloro-2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt (1.25 g, 3.5 mmol) with [2-N-(benzyloxycarbonyl)-guanin-9-yl]-acetic acid (1.15 g, 3.5 mmol) as per the procedure of example 82. 1H NMR (DMSO-d6): δ 11.46 (s, 1H), 11.37 (s, 1H), 8.44˜8.31 (m, 2H), 8.09 (m, 1H), 7.82 (s, 0.6H), 7.78 (s, 0.4H), 7.46˜7.33 (m, 5H), 5.25 (s, 2H), 5.12 (s, 1.2H), 5.04 (s, 0.8H), 4.51 (s, 0.8H), 4.26 (s, 1.21H), 4.10˜4.00 (m, 2.4H), 3.92˜3.82 (m, 1.6H).

Sources & evidence

ORD record
ord-6bc60fd607e048fbb26989487b430f02
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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