Phosgene → 4,5-Bis-(4-chloro-phenyl)-2-(4-ethoxy-2-trifluoromethyl-pyrimidin-5-yl)-4,5-dihydro-imidazole-1-carbonyl chloride

HRID 645730Notes

Reaction equation

HRID 645730 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[C:21]([O:30][CH2:31][CH3:32])=[N:22][C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][CH:25]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:33](Cl)([Cl:35])=[O:34]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:11]([C:33]([Cl:35])=[O:34])[C:10]([C:20]3[C:21]([O:30][CH2:31][CH3:32])=[N:22][C:23]([C:26]([F:27])([F:29])[F:28])=[N:24][CH:25]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 866136254,5-bis-(4-chloro-phenyl)-2-(4-ethoxy-2-trifluoromethyl-pyrimidin-5-yl)-4,5-dihydro-1H-imidazole

Product 1

HCID 866136244,5-Bis-(4-chloro-phenyl)-2-(4-ethoxy-2-trifluoromethyl-pyrimidin-5-yl)-4,5-dihydro-imidazole-1-carbonyl chloride

Procedure

Using the procedure as described in example 1, cis-4-[4,5-bis-(4-chloro-phenyl)-2-(4-ethoxy-2-trifluoromethyl-pyrimidin-5-yl)-4,5-dihydro-1H-imidazole was reacted with phosgene to give cis-4-[4,5-bis-(4-chloro-phenyl)-2-(4-ethoxy-2-trifluoromethyl-pyrimidin-5-yl)-4,5-dihydro-imidazole-1-carbonyl chloride. The carbonyl chloride was then coupled with 2-piperazinone to give cis-4-[4,5-bis-(4-chloro-phenyl)-2-(4-ethoxy-2-trifluoromethyl-pyrimidin-5-yl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one. HR-MS (ES, m/z) calculated for C27H24N6O3F3Cl2 [(M+H)+] 607.1234, observed 607.1231.

Sources & evidence

ORD record
ord-9546032fcdf24a24a3f04aa4f5e21ce8
Source dataset
uspto-grants-2010_04
Patent number
US07705007B2

Reaction notes

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