Dimethylamine → HCID 59792779, compound

HRID 31517Notes

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)[N:11]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:31])[CH2:29]Cl)[CH2:24][CH2:23]3)=[O:21])[C:10]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][C:33]=3[O:42][CH2:43][CH3:44])=[N:9]2)=[CH:4][CH:3]=1.[CH:45]([N:48](C(C)C)[CH2:49]C)(C)C.CNC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][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:20]([N:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:31])[CH2:29][N:48]([CH3:49])[CH3:45])[CH2:24][CH2:23]3)=[O:21])[C:10]([C:32]3[CH:37]=[CH:36][C:35]([C:38]([F:40])([F:39])[F:41])=[CH:34][C:33]=3[O:42][CH2:43][CH3:44])=[N:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-{4-[4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-2-chloro-ethanone (9.65 mg) and diisopropylethylamine (5 uL) was added dimethylamine (50 uL, 2.0M solution in tetrahydrofuran). The reaction mixture was capped and heated at 60° C. overnight. It was diluted with methylene chloride and washed with water. The organic layer was concentrated to dryness to give 1-{4-[4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-2-dimethylamino-ethanone (9.17 mg, 92% yield). LR-MS: 677.3 [(M+H)+].

Workup

customThe reaction mixture was capped
washwashed with water
concentrationThe organic layer was concentrated to dryness

Sources & evidence

ORD record: ord-061c7e4912a64446858f27954cdecd17
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425638B2

Reaction notes

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