rac-(4S,5R)-2-(4-Chloro-2-ethoxy-5-methanesulfonyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride → [(4S,5R)-2-(4-Chloro-2-ethoxy-5-methanesulfonyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-[4-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-piperazin-1-yl]-methanone

Participants

Role	Name	HCID	Charge
Reactant	rac-(4S,5R)-2-(4-Chloro-2-ethoxy-5-methanesulfonyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride	HCID 53628802	—
Reactant	4-(Piperazin-1-yl)-1lambda6-thiane-1,1-dione dihydrochloride	HCID 56773490	—
Product	[(4S,5R)-2-(4-Chloro-2-ethoxy-5-methanesulfonyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazol-1-yl]-[4-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-piperazin-1-yl]-methanone	HCID 58894291	—

Reaction Steps

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(4-chloro-2-ethoxy-5-methanesulfonyl-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 61) was reacted with 1-(1,1-dioxo-tetrahydro-2H-thiopyran-4-yl)-piperazine dihydrochloride (example 22) to give the title compound as a racemic mixture. The enantiomers were separated by supercritical fluid chromatography (Berger Instrument Multi-Gram II, Regis Technologies Whelk-01 3×25 cm, 35° C. at 100 bar, eluting with 40% methanol in carbon dioxide) gave the title compound. HR-MS (ES, m/z) calculated for C36H42N4O6S2Cl3 [(M+H)+] 795.1606, observed 795.1605.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07851626B2
Source dataset	uspto-grants-2010_12
ORD ID	ord-d3f045ff09f443db8f5b84544dff756f
Source note	uspto-grants-2010_12