2-(Piperazin-1-yl)acetamide dihydrochloride → 2-{4-[(4S,5R)-2-(5-tert-Butylsulfamoyl-4-chloro-2-ethoxyphenyl)-4,5-bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl]-piperazin-1-yl}-acetamide

HRID 2263933Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:54])[C@:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[N:11]([C:21](N3CCN(CCCS(C)(=O)=O)CC3)=[O:22])[C:10]([C:36]3[C:37]([O:51][CH2:52][CH3:53])=[CH:38][C:39]([Cl:50])=[C:40]([S:42]([NH:45][C:46]([CH3:49])([CH3:48])[CH3:47])(=[O:44])=[O:43])[CH:41]=3)=[N:9]2)=[CH:4][CH:3]=1.Cl.Cl.[N:57]1([CH2:63][C:64]([NH2:66])=[O:65])[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1>>[C:46]([NH:45][S:42]([C:40]1[C:39]([Cl:50])=[CH:38][C:37]([O:51][CH2:52][CH3:53])=[C:36]([C:10]2[N:11]([C:21]([N:60]3[CH2:61][CH2:62][N:57]([CH2:63][C:64]([NH2:66])=[O:65])[CH2:58][CH2:59]3)=[O:22])[C@@:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[C@@:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)([CH3:54])[N:9]=2)[CH:41]=1)(=[O:43])=[O:44])([CH3:47])([CH3:48])[CH3:49]

Participants

Reactant 2

HCID 177503752-(Piperazin-1-yl)acetamide dihydrochloride

HCID 588943015-{(4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-[4-(3-methanesulfonyl-propyl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-N-tert-butyl-2-chloro-4-ethoxy-benzenesulfonamide

Product 1

HCID 588942512-{4-[(4S,5R)-2-(5-tert-Butylsulfamoyl-4-chloro-2-ethoxyphenyl)-4,5-bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl]-piperazin-1-yl}-acetamide

Procedure

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(5-tert-butylsulfamoyl-4-chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 45) 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 25% of 1:1 acetonitrile/ethanol in carbon dioxide). HR-MS (ES, m/z) calculated for C36H44N6O5SCl3 [(M+H)+] 777.2154, observed 777.2146.

Sources & evidence

ORD record: ord-d69e986b0c694181818789498328eac7
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851626B2

Reaction notes

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