Cyclopentanecarbonyl chloride → N-[6-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]cyclopentanecarboxamide

HRID 1994409Notes

Reaction equation

[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][CH:10]1[C:15](=[O:16])[N:14]2[CH:17]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:18](=[O:24])[N:19]([CH:21]([CH3:23])[CH3:22])[CH2:20][CH:13]2[N:12]([S:33]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:37]=2[Cl:43])(=[O:35])=[O:34])[CH2:11]1>>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH:17]2[N:14]3[C:15](=[O:16])[CH:10]([NH:9][C:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[O:7])[CH2:11][N:12]([S:33]([C:36]4[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:37]=4[Cl:43])(=[O:35])=[O:34])[CH:13]3[CH2:20][N:19]([CH:21]([CH3:23])[CH3:22])[C:18]2=[O:24])=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 78284Cyclopentanecarbonyl chloride

HCID 591342523-Amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

Product 1

HCID 59134153N-[6-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]cyclopentanecarboxamide

Procedure

Synthesis took place in analogy to Example 22 using cyclopentanecarbonyl chloride and 3-amino-6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione. The desired product is obtained with MW=654.12 (calculated, monoisotopic); measured value (M+H)+: 655.1

Workup

customSynthesis

Sources & evidence

ORD record: ord-8aa3c0da2f11479da6b03e601dc41e1c
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652007B2

Reaction notes

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