2-(Piperazin-1-yl)acetamide dihydrochloride → 2-{4-[(4S,5R)-2-(4-tert-Butylsulfamoyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-acetamide
Reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([C:36](Cl)=[O:37])[C:17]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)([CH3:28])[C:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)([CH3:20])[N:19]=2)=[C:11]([O:39][CH2:40][CH3:41])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[N:44]1([CH2:50][C:51]([NH2:53])=[O:52])[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([C:36]([N:47]3[CH2:48][CH2:49][N:44]([CH2:50][C:51]([NH2:53])=[O:52])[CH2:45][CH2:46]3)=[O:37])[C@@:17]([C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)([CH3:28])[C@@:18]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)([CH3:20])[N:19]=2)=[C:11]([O:39][CH2:40][CH3:41])[CH:10]=1)(=[O:7])=[O:8])([CH3:3])([CH3:2])[CH3:4]Participants
3
Reactant 2
Product 1
Procedure
In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(4-tert-butylsulfamoyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with 2-piperazin-1-yl-acetamide dihydrochloride (Matrix Scientific) 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 35% methanol in carbon dioxide). HR-MS (ES, m/z) calculated for C36H44N6O5SCl2 [(M+H)+] 743.2544, observed 743.2538.
Sources & evidence
- ORD record
- ord-fe1be688817e42939a949e008d1e4d22
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851626B2
Reaction notes
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