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Sodium hydride → 1-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(difluoromethyl)-1,3-thiazol-2-yl)methoxy)pyridin-2(1H)-one

HRID 2203110
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인쇄 미리보기

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HRID 2203110 반응식
[F:1][CH:2]([F:10])[C:3]1[N:4]=[C:5]([CH2:8][OH:9])[S:6][CH:7]=1.Br[C:12]1[CH:17]=[CH:16][N:15]([C:18]2[CH:19]=[CH:20][C:21]3[N:25]=[C:24]([CH:26]4[CH2:28][CH2:27]4)[N:23]([CH3:29])[C:22]=3[CH:30]=2)[C:14](=[O:31])[CH:13]=1.[H-].[Na+].CC(N(C)C)=O>O>[CH:26]1([C:24]2[N:23]([CH3:29])[C:22]3[CH:30]=[C:18]([N:15]4[CH:16]=[CH:17][C:12]([O:9][CH2:8][C:5]5[S:6][CH:7]=[C:3]([CH:2]([F:10])[F:1])[N:4]=5)=[CH:13][C:14]4=[O:31])[CH:19]=[CH:20][C:21]=3[N:25]=2)[CH2:27][CH2:28]1
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참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 680963792-Thiazolemethanol, 4-(difluoromethyl)-HCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

생성물 1

HCID 896910071-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-(difluoromethyl)-1,3-thiazol-2-yl)methoxy)pyridin-2(1H)-one수율 19.7%

시약·촉매·용매

1
HCID 962Water용매

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온도
120 °C

실험 절차

A mixture of (4-(difluoromethyl)-1,3-thiazol-2-yl)methanol (50 mg), 4-bromo-1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-2(1H)-one (69.5 mg), NaH (60% in oil, 12.1 mg) and DMA (1 ml) was heated at 120° C. under microwave irradiation for 2 h. The mixture was poured into water and extracted with EtOAc. The extract 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 (17 mg) as a white solid.

후처리

  1. extractionextracted with EtOAc
  2. washThe extract 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-0ea125f01e2b47f7ac6140b61cc78057
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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