1-(3-(Methylsulfonyl)propyl)piperazine dihydrochloride → HCID 58894261, compound

HRID 2264031Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:35][CH2:36][CH3:37])=[C:9]([C:11]2[N:12]([C:32](Cl)=[O:33])[C:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[CH3:40][S:41]([CH2:44][CH2:45][CH2:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)(=[O:43])=[O:42]>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:35][CH2:36][CH3:37])=[C:9]([C:11]2[N:12]([C:32]([N:50]3[CH2:51][CH2:52][N:47]([CH2:46][CH2:45][CH2:44][S:41]([CH3:40])(=[O:42])=[O:43])[CH2:48][CH2:49]3)=[O:33])[C@@:13]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 498534791-(3-(Methylsulfonyl)propyl)piperazine dihydrochloride

HCID 86612884HCID 86612884, compound

Product 1

HCID 58894261HCID 58894261, compound

Procedure

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(5-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with 1-(3-methanesulfonyl-propyl)-piperazine dihydrochloride (prepared as described in Fotouhi, N. et al. WO 2005110996) to give the title compound as a racemic mixture. The enantiomers were separated by supercritical fluid chromatography (Berger Instrument Multi-Gram II, Daicel ChiralPak OD-H 3×25 cm, 35° C. at 100 bar, eluting with 20% of 1:1 ethanol/acetonitrile in carbon dioxide) gave the title compound. HR-MS (ES, m/z) calculated for C38H49N4O4SCl2 [(M+H)+] 727.2846, observed 727.2847.

Sources & evidence

ORD record: ord-7a3f7aa7a67b484693906b93ec50d305
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851626B2

Reaction notes

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