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Dimethylformamide → 4-(1-Benzothiophen-5-ylmethoxy)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203082
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HRID 2203082 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([CH:16]4[CH2:18][CH2:17]4)[N:13]([CH3:19])[C:12]=3[CH:20]=2)[C:4](=[O:21])[CH:3]=1.[S:22]1[CH:26]=[CH:25][C:24]2[CH:27]=[C:28]([CH2:31][OH:32])[CH:29]=[CH:30][C:23]1=2.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[S:22]1[C:23]2[CH:30]=[CH:29][C:28]([CH2:31][O:32][C:2]3[CH:7]=[CH:6][N:5]([C:8]4[CH:9]=[CH:10][C:11]5[N:15]=[C:14]([CH:16]6[CH2:18][CH2:17]6)[N:13]([CH3:19])[C:12]=5[CH:20]=4)[C:4](=[O:21])[CH:3]=3)=[CH:27][C:24]=2[CH:25]=[CH:26]1
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27954461-Benzothiophen-5-ylmethanolHCID 896909614-Chloro-1-(2-cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-2(1h)-pyridinone

생성물 1

HCID 897025834-(1-Benzothiophen-5-ylmethoxy)-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one수율 10.5%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-chloro-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (100 mg), benzo[b]thiophen-5-ylmethanol (110 mg), cesium carbonate (326 mg) and DMF (3 ml) was heated at 100° C. overnight. The mixture was poured into water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, concentrated in vacuo, and purified by NH silica gel column chromatography (hexane/EtOAc) to give the title compound (15 mg) as a white solid.

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by NH silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-9023b02b03ce4789bbaca7cb32156fc0
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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