Potassium Carbonate → N-(3,4-Dimethyl-phenyl)-2-(2-methyl-benzoimidazol-1-yl)-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094369

반응식

HRID 1094369 반응식
Br[CH2:2][C:3]([N:5]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([CH3:25])[CH:19]=1)[CH2:6][CH2:7][C:8]1[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=1)=[O:4].[CH3:26][C:27]1[NH:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CC(OC)(C)C>[CH3:25][C:20]1[CH:19]=[C:18]([N:5]([CH2:6][CH2:7][C:8]2[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=2)[C:3](=[O:4])[CH2:2][N:28]2[C:29]3[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=3[N:31]=[C:27]2[CH3:26])[CH:23]=[CH:22][C:21]=1[CH3:24]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 119842-MethylbenzimidazoleHCID 580076022-Bromo-N-(3,4-dimethyl-phenyl)-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

생성물 1

HCID 58007562N-(3,4-Dimethyl-phenyl)-2-(2-methyl-benzoimidazol-1-yl)-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide수율 57.6%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 15413tert-Butyl methyl ether용매

실험 절차

A suspension of 2-bromo-N-(3,4-dimethyl-phenyl)-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide (134 mg, 0.32 mmol), 2-methylbenzimidazole (85 mg, 0.65 mmol) and potassium carbonate (67 mg, 0.48 mmol) in acetonitrile (1 mL) was irradiated in the microwave for 20 min. at 140° C. The reaction mixture was diluted with TBME (15 mL) and washed with water (15 mL) and brine (15 mL). The aqueous layers were extracted with tert-butylmethylether (15 mL) and the combined organic layers dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate:methanol=50:50:0 to 0:95:5) afforded the title compound (86 mg, 57%) as a light brown oil. MS m/e: 467.0 [M+H]+.

후처리

  1. customwas irradiated in the microwave for 20 min. at 140° C
  2. washwashed with water (15 mL) and brine (15 mL)
  3. extractionThe aqueous layers were extracted with tert-butylmethylether (15 mL)
  4. dry with materialthe combined organic layers dried over sodium sulfate
  5. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate:methanol=50:50:0 to 0:95:5)

출처 및 근거

ORD 기록
ord-5dea96a9abae47d3822c509a9a2e4f81
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133909B2

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