1-(3-(Methylsulfonyl)propyl)piperazine dihydrochloride → HCID 86612881, compound
Reaction equation
C(C1C(Cl)=CC(C2NC(C3C=CC(Cl)=CC=3)(C)C(C3C=CC(Cl)=CC=3)(C)N=2)=[C:7]([O:33]CC)C=1)(C)(C)C.Cl.Cl.[CH3:38][S:39]([CH2:42][CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1)(=[O:41])=[O:40]>>[CH3:38][S:39]([CH2:42][CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][N:48]([CH:7]=[O:33])[CH2:47][CH2:46]1)(=[O:40])=[O:41]Participants
Procedure
In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(4-tert-butyl-5-chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole was reacted with 1-(3-methanesulfonyl-propyl)-piperazine dihydrochloride (prepared as described in Fotouhi, N. et al. WO 2005110996) to give the racemic rac-(4S*,5R*)-2-(4-tert-butyl-5-chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-[4-(3-methanesulfonyl-propyl)-piperazin-1-yl]-methanone. Chiral separation of the enantiomers by supercritical fluid chromatography (Berger Instrument Multi-Gram II, Daicel ChiralPak OD-H 3×25 cm, 35° C. at 100 bar, eluting with 25% methanol in carbon dioxide) gave the title compound. HR-MS (ES, m/z) calculated for C38H48N4O4SCl3 [(M+H)+] 761.2457, observed 761.2460.
Sources & evidence
- ORD record
- ord-7d64b62032db45cf94cbb77cf6b49df6
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851626B2
Reaction notes
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