Diisopropylethylamine → 3-{4-[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-propionitrile

HRID 31514

반응식

HRID 31514 반응식
Br[CH:2]([CH3:5])[C:3]#[N:4].Cl.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[N:17]([C:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[O:27])[C:16]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][C:35]=3[O:44][CH2:45][CH3:46])=[N:15]2)=[CH:10][CH:9]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[CH:18]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[N:17]([C:26]([N:28]3[CH2:33][CH2:32][N:31]([CH2:5][CH2:2][C:3]#[N:4])[CH2:30][CH2:29]3)=[O:27])[C:16]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([F:41])([F:43])[F:42])=[CH:36][C:35]=3[O:44][CH2:45][CH3:46])=[N:15]2)=[CH:12][CH:13]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 1405382-BromopropionitrileHCID 86595528[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-(piperazin-1-yl)-methanone hydrochloride

생성물 1

HCID 111815003-{4-[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-propionitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Bromopropionitrile (10 uL, 0.120 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 hydrochloride and diisopropylethylamine (42 uL, 0.240 mmol) in dimethylformamide (1.0 mL). The reaction was stirred at room temperature overnight. Evaporation of the solvent and purification of the crude residue by flash chromatography over silica gel using 1-2% methanol in methylene chloride gave 3-{4-[4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-propionitrile, which was dissolved in dilute hydrochloric acid (0.5 N, 1 mL) and lyophilized to give 3-{4-[4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-propionitrile hydrochloride as an off-white powder (20 mg, 39% yield). LR-MS (APCI): 644.4 [(M+H)+].

후처리

  1. customEvaporation of the solvent and purification of the crude residue by flash chromatography over silica gel using 1-2% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-351c28caa80a42c4b0114a9bcfdce508
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425638B2

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