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

反応式

HRID 31523 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)+].

後処理

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

出典と根拠

ORDレコード
ord-ca16100f561a4a5f9140a1b52122e918
出典データセット
uspto-grants-2008_09
特許番号
US07425638B2

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