(6-{[(Diphenylmethoxy)carbonyl]amino}-9H-purin-9-yl)acetic acid → 4-{[6-N-(Benzhydryloxycarbonyl)-adenin-9-yl]-acetyl}-1-(4-fluoro-2-nitro-benzenesulfonyl)-piperazin-2-one

HRID 1794957Notes

Reaction equation

HRID 1794957 reaction equation
Cl.[F: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[N:47]=[CH:46][N:45]=[C:44]2[C:40]=1[N:41]=[CH:42][N:43]2[CH2:48][C:49](O)=[O:50])=[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[N:47]=[CH:46][N:45]=[C:44]2[C:40]=1[N:41]=[CH:42][N:43]2[CH2:48][C:49]([N:15]1[CH2:16][CH2:17][N:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][C:5]=2[N+:19]([O-:21])=[O:20])(=[O:11])=[O:10])[C:13](=[O:18])[CH2:14]1)=[O:50])=[O:37])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 15513044(6-{[(Diphenylmethoxy)carbonyl]amino}-9H-purin-9-yl)acetic acidHCID 68799248HCID 68799248, compound

Product 1

HCID 222224074-{[6-N-(Benzhydryloxycarbonyl)-adenin-9-yl]-acetyl}-1-(4-fluoro-2-nitro-benzenesulfonyl)-piperazin-2-oneYield 58.4%

Procedure

The title compound (805 mg, 58%) was synthesized by reaction of 1-(4-fluoro-2-nitro-benzenesulfonyl)-piperazin-2-one HCl salt (679 mg, 2.0 mmol) with [6-N-(benzhydryloxycarbonyl)-adenin-9-yl]-acetic acid (807 mg, 2.0 mmol) as per the procedure of example 73. 1H NMR (DMSO-d6) δ 10.95 (s, 1H), 8.59 (s, 0.6H), 8.58 (s, 0.4H), 8.47˜8.40 (m, 1H), 8.33 (s, 0.6H), 8.30 (s, 0.4H), 8.26 (m, 1H), 7.88 (m, 1H), 7.53˜7.27 (m, 10H), 6.82 (s, 1H), 5.38 (s, 1.2H), 5.30 (s, 0.8H), 4.56 (s, 0.8H), 4.27 (s, 1.2H), 4.12˜4.06 (m, 2.4H), 3.91˜3.85 (br. m, 1.6H).

Sources & evidence

ORD record
ord-93d3b7c25c5845169e57db320d5df24d
Source dataset
uspto-grants-2006_04
Patent number
US07022851B2

Reaction notes

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