1-(3-(Methylsulfonyl)propyl)piperazine dihydrochloride → HCID 86612881, compound
Reaction equation
ClC1C=CC(C2(C)C(C3C=CC(Cl)=CC=3)(C)N([C:21](Cl)=[O:22])C(C3C=CC(C(F)(F)F)=CC=3OCC)=N2)=CC=1.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]>>[CH3:40][S:41]([CH2:44][CH2:45][CH2:46][N:47]1[CH2:52][CH2:51][N:50]([CH:21]=[O:22])[CH2:49][CH2:48]1)(=[O:42])=[O:43]Participants
Procedure
In a manner analogous to the method described in example 5, rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-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 racemic rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-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 C35H40N4O4SF3Cl2 [(M+H)+] 739.2094, observed 739.2094.
Sources & evidence
- ORD record
- ord-ceddf40e28bb4fd7b1864172aedefee8
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851626B2
Reaction notes
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