1-(3-(Methylsulfonyl)propyl)piperazine dihydrochloride → 3-(4-{4,5-Bis-(4-chloro-phenyl)-1-[4-(3-methanesulfonyl-propyl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-3-methyl-butan-2-one

HRID 2264014Notes

Reaction equation

HRID 2264014 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:39])[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]=[CH:28][C:27]([C:30]([CH3:35])([CH3:34])[C:31](=[O:33])[CH3:32])=[CH:26][C:25]=3[O:36][CH2:37][CH3:38])=[N:9]2)=[CH:4][CH:3]=1.Cl.Cl.[CH3:42][S:43]([CH2:46][CH2:47][CH2:48][N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1)(=[O:45])=[O:44]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:39])[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:52]3[CH2:53][CH2:54][N:49]([CH2:48][CH2:47][CH2:46][S:43]([CH3:42])(=[O:44])=[O:45])[CH2:50][CH2:51]3)=[O:22])[C:10]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:35])([CH3:34])[C:31](=[O:33])[CH3:32])=[CH:26][C:25]=3[O:36][CH2:37][CH3:38])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 498534791-(3-(Methylsulfonyl)propyl)piperazine dihydrochlorideHCID 72455723rac-(4S*,5R*)-4,5-Bis-(4-chloro-phenyl)-2-[4-(1,1-dimethyl-2-oxo-propyl)-2-ethoxy-phenyl]-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

Product 1

HCID 670713433-(4-{4,5-Bis-(4-chloro-phenyl)-1-[4-(3-methanesulfonyl-propyl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-3-ethoxy-phenyl)-3-methyl-butan-2-one

Procedure

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-[4-(1,1-dimethyl-2-oxo-propyl)-2-ethoxy-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 product 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 25% methanol in carbon dioxide). HR-MS (ES, m/z) calculated for C39H49N4O5SCl2 [(M+H)+] 775.2795, observed 775.2795.

Sources & evidence

ORD record
ord-4d1fcbde9738493e868d146965cb3f8e
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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