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Water → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-2-thienyl)methoxy)pyridin-2(1H)-one

HRID 2203102
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HRID 2203102 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH2:8][OH:9])[S:6][CH:7]=1.[H-].[Na+].Br[C:15]1[CH:20]=[CH:19][N:18]([C:21]2[CH:22]=[CH:23][C:24]3[N:28]=[C:27]([CH:29]4[CH2:31][CH2:30]4)[N:26]([CH3:32])[C:25]=3[CH:33]=2)[C:17](=[O:34])[CH:16]=1.O>CC(N(C)C)=O>[CH:29]1([C:27]2[N:26]([CH3:32])[C:25]3[CH:33]=[C:21]([N:18]4[CH:19]=[CH:20][C:15]([O:9][CH2:8][C:5]5[S:6][CH:7]=[C:3]([C:2]([F:10])([F:1])[F:11])[CH:4]=5)=[CH:16][C:17]4=[O:34])[CH:22]=[CH:23][C:24]=3[N:28]=2)[CH2:30][CH2:31]1
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6

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HCID 962WaterHCID 24758Sodium hydrideHCID 896902462-Thiophenemethanol, 4-(trifluoromethyl)-HCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

생성물 1

HCID 896909571-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(trifluoromethyl)-2-thienyl)methoxy)pyridin-2(1H)-one수율 15%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
120 °C

실험 절차

To a solution of (4-(trifluoromethyl)thiophen-2-yl)methanol (50 mg) in DMA (2 ml) was added NaH (60% in oil, 18.3 mg) at room temperature, and the mixture was stirred for 30 min. 4-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (79 mg) was added to the mixture, and the mixture was heated at 120° C. for 30 min under microwave irradiation. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with saturated NaHCO3 solution and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/MeOH), followed by crystallized from hot EtOAc to give the title compound (15.3 mg) as pale yellow crystals.

후처리

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with saturated NaHCO3 solution and brine successively
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (EtOAc/MeOH)
  7. customby crystallized from hot EtOAc

출처 및 근거

ORD 기록
ord-a668cd8036fd42ba93d3cc905545f5c3
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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