Triethylamine → [4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-(2-hydroxy-2-trifluoromethyethyl)-piperazin-1-yl]-methanone

HRID 31523

반응식

HRID 31523 반응식
[F:1][C:2]([F:7])([F:6])[CH:3]1[O:5][CH2:4]1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:18]([C:27]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[O:28])[C:17]([C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:36]=3[O:45][CH2:46][CH3:47])=[N:16]2)=[CH:11][CH:10]=1.C(N(CC)CC)C>CO>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[CH:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:18]([C:27]([N:29]3[CH2:34][CH2:33][N:32]([CH2:4][CH:3]([OH:5])[C:2]([F:7])([F:6])[F:1])[CH2:31][CH2:30]3)=[O:28])[C:17]([C:35]3[CH:40]=[CH:39][C:38]([C:41]([F:43])([F:42])[F:44])=[CH:37][C:36]=3[O:45][CH2:46][CH3:47])=[N:16]2)=[CH:13][CH:14]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 5207692-(Trifluoromethyl)oxiraneHCID 69272507[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[piperazin-1-yl]-methanone

생성물 1

HCID 11193479[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-(2-hydroxy-2-trifluoromethyethyl)-piperazin-1-yl]-methanone

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1,1,1-trifluoro-2,3-epoxypropane (9 uL, 0.10 mmol) was added to a mixture of [4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[piperazin-1-yl]-methanone (30 mg, 0.048 mmol) and triethylamine (20 uL, 0.144 mmol) in anhydrous methanol (1.0 mL). The reaction was stirred overnight. Evaporation of the solvent and chromatography of the residue over silica gel using 0-5% methanol in methylene chloride gave [4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-(2-hydroxy-2-trifluoromethyethyl)-piperazin-1-yl]-methanone, which was dissolved in dilute hydrochloric acid (0.5 N, 1 mL) and lyophilized to give [4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-[4-(2-hydroxy-2-trifluoromethyethyl)-piperazin-1-yl]-methanone hydrochloride as an off-white powder (38 mg, 84%). LR-MS (APCI): 703.5 [(M+H)+].

후처리

  1. customEvaporation of the solvent and chromatography of the residue over silica gel using 0-5% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-ca16100f561a4a5f9140a1b52122e918
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425638B2

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