n,n-Dimethylpiperazine-1-carboxamide → 4-[2-(2-tert-Butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperazine-1-carboxylic acid dimethylamide

HRID 1894332Notes

Reaction equation

[C:1]([C:5]1[N:10]=[C:9]([O:11][CH2:12][CH3:13])[C:8]([C:14]2[N:15]([C:35](Cl)=[O:36])[C:16]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)([CH3:27])[C:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)([CH3:19])[N:18]=2)=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:38][N:39]([CH3:48])[C:40]([N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1)=[O:41]>>[CH3:38][N:39]([CH3:48])[C:40]([N:42]1[CH2:43][CH2:44][N:45]([C:35]([N:15]2[C:16]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)([CH3:27])[C:17]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)([CH3:19])[N:18]=[C:14]2[C:8]2[C:9]([O:11][CH2:12][CH3:13])=[N:10][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[N:6][CH:7]=2)=[O:36])[CH2:46][CH2:47]1)=[O:41]

Participants

Reactant 2

HCID 712909n,n-Dimethylpiperazine-1-carboxamide

HCID 76588520rac-(4S*,5R*)-2-(2-tert-butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride

Product 1

HCID 252624264-[2-(2-tert-Butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperazine-1-carboxylic acid dimethylamide

Procedure

In a manner analogous to the method described in example 3, rac-(4S*,5R*)-2-(2-tert-butyl-4-ethoxy-pyrimidin-5-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with piperazine-1-carboxylic acid dimethylamide (Oakwood) to give the title compound. HR-MS (ES, m/z) calculated for C35H44N7O3Cl2 [(M+H)+] 680.2877, observed 680.288.

Sources & evidence

ORD record: ord-8d7412610f3c47b8bce38d5c25c99a8a
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513239B2

Reaction notes

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