methyl (2S)-1-methylpiperazine-2-carboxylate → (S)-4-[(4S,5R)-2-(4-tert-Butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-1-methyl-piperazine-2-carboxylic acid methyl ester

HRID 2263893Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:32](Cl)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:35][CH2:36][CH3:37])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:38][O:39][C:40]([C@@H:42]1[CH2:47][NH:46][CH2:45][CH2:44][N:43]1[CH3:48])=[O:41]>>[CH3:38][O:39][C:40]([C@@H:42]1[CH2:47][N:46]([C:32]([N:12]2[C@@:13]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=[C:11]2[C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=2[O:35][CH2:36][CH3:37])=[O:33])[CH2:45][CH2:44][N:43]1[CH3:48])=[O:41]

Participants

Reactant 2

HCID 29920832methyl (2S)-1-methylpiperazine-2-carboxylate

HCID 58894207(4S,5R)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

Product 1

HCID 17754847(S)-4-[(4S,5R)-2-(4-tert-Butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-1-methyl-piperazine-2-carboxylic acid methyl ester

Procedure

In a manner analogous to the method described in example 5, (4S,5R)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 4) was reacted with (S)-1-methyl-piperazine-2-carboxylic acid methyl ester (Aldrich) to give the title compound. HR-MS (ES, m/z) calculated for C37H45N4O4Cl2 [(M+H)+] 679.2813, observed 679.2805.

Sources & evidence

ORD record: ord-b3e3b4b7d1b6404499f0e4387573f137
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851626B2

Reaction notes

Loading…