1-(3-(Methylsulfonyl)propyl)piperazine dihydrochloride → {(4S,5R)-4,5-Bis-(4-chlorophenyl)-2-[2-ethoxy-4-methoxy-5-(pyrrolidine-1-sulfonyl)-phenyl]-4,5-dimethyl-4,5-dihydroimidazol-1-yl}-[4-(3-methanesulfonylpropyl)-piperazin-1-yl]methanone

HRID 2263942Notes

Reaction equation

HRID 2263942 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:43])[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[N:11]([C:21](Cl)=[O:22])[C:10]([C:24]3[CH:29]=[C:28]([S:30]([N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)(=[O:32])=[O:31])[C:27]([O:38][CH3:39])=[CH:26][C:25]=3[O:40][CH2:41][CH3:42])=[N:9]2)=[CH:4][CH:3]=1.Cl.Cl.[CH3:46][S:47]([CH2:50][CH2:51][CH2:52][N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)(=[O:49])=[O:48]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]2([CH3:43])[C@:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[N:11]([C:21]([N:56]3[CH2:55][CH2:54][N:53]([CH2:52][CH2:51][CH2:50][S:47]([CH3:46])(=[O:48])=[O:49])[CH2:58][CH2:57]3)=[O:22])[C:10]([C:24]3[CH:29]=[C:28]([S:30]([N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)(=[O:32])=[O:31])[C:27]([O:38][CH3:39])=[CH:26][C:25]=3[O:40][CH2:41][CH3:42])=[N:9]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 498534791-(3-(Methylsulfonyl)propyl)piperazine dihydrochlorideHCID 72455718rac-(4S*,5R*)-4,5-Bis-(4-chlorophenyl)-2-[2-ethoxy-4-methoxy-5-(pyrrolidine-1-sulfonyl)-phenyl]-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl chloride

Product 1

HCID 17754457{(4S,5R)-4,5-Bis-(4-chlorophenyl)-2-[2-ethoxy-4-methoxy-5-(pyrrolidine-1-sulfonyl)-phenyl]-4,5-dimethyl-4,5-dihydroimidazol-1-yl}-[4-(3-methanesulfonylpropyl)-piperazin-1-yl]methanone

Procedure

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-4,5-bis-(4-chlorophenyl)-2-[2-ethoxy-4-methoxy-5-(pyrrolidine-1-sulfonyl)-phenyl]-4,5-dimethyl-4,5-dihydroimidazole-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 then separated by supercritical fluid chromatography (Berger Instrument Multi-Gram II, Daicel ChiralPak OD-H 3×25 cm, 35° C. at 100 bar, eluting with 30% methanol in carbon dioxide). HR-MS (ES, m/z) calculated for C39H50N5O7S2Cl2 [(M+H)+] 834.2523, observed 834.2524.

Sources & evidence

ORD record
ord-09bf7f3402ac4cabaa4345b4c95c1da6
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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