methyl (2S)-1-methylpiperazine-2-carboxylate → (S)-4-[(4S,5R)-2-(5-tert-Butylsulfamoyl-4-chloro-2-ethoxyphenyl)-4,5-bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl]-1-methylpiperazine-2-carboxylic acid methyl ester

HRID 2263934Notes

Reaction equation

HRID 2263934 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]([N:23]3[CH2:28][CH2:27][N:26]([CH2:29]CCS(C)(=O)=O)[CH2:25][CH2:24]3)=[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.[CH3:55][O:56][C:57]([C@@H]1CNCCN1C)=[O:58]>>[CH3:55][O:56][C:57]([C@@H:25]1[CH2:24][N:23]([C:21]([N:11]2[C@@:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=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]=[C:10]2[C:36]2[CH:41]=[C:40]([S:42](=[O:44])(=[O:43])[NH:45][C:46]([CH3:48])([CH3:49])[CH3:47])[C:39]([Cl:50])=[CH:38][C:37]=2[O:51][CH2:52][CH3:53])=[O:22])[CH2:28][CH2:27][N:26]1[CH3:29])=[O:58]

Participants

3

Reactant 2

HCID 29920832methyl (2S)-1-methylpiperazine-2-carboxylateHCID 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 58894271(S)-4-[(4S,5R)-2-(5-tert-Butylsulfamoyl-4-chloro-2-ethoxyphenyl)-4,5-bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl]-1-methylpiperazine-2-carboxylic acid methyl ester

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 (S)-1-methyl-piperazine-2-carboxylic acid methyl ester 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% methanol in carbon dioxide). HR-MS (ES, m/z) calculated for C37H45N5O6SCl3 [(M+H)+] 792.2151, observed 792.2148.

Sources & evidence

ORD record
ord-6d7d5e4712244b97aa74499bbceadd2c
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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