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

HRID 2203119
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HRID 2203119 반응식
[F:1][CH:2]([F:10])[C:3]1[S:4][CH:5]=[C:6]([CH2:8][OH:9])[N:7]=1.Cl[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.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[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:6]5[N:7]=[C:3]([CH:2]([F:10])[F:1])[S:4][CH:5]=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

5

반응물 3

HCID 23665647Potassium tert-butoxideHCID 89690005[2-(Difluoromethyl)-1,3-thiazol-4-yl]methanolHCID 896909614-Chloro-1-(2-cyclopropyl-1-methyl-1h-benzimidazol-6-yl)-2(1h)-pyridinone

생성물 1

HCID 896909561-(2-Cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-((2-(difluoromethyl)-1,3-thiazol-4-yl)methoxy)pyridin-2(1H)-one수율 50.2%

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
100 °C

실험 절차

To a suspension of (2-(difluoromethyl)thiazol-4-yl)methanol (44 mg) and 4-chloro-1-(2-cyclopropyl-1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-2(1H)-one (66.5 mg) in toluene (1 ml) was added potassium tert-butoxide (49.8 mg) at 100° C., and the mixture was stirred at 100° C. under dry atmosphere (CaCl2 tube) for 30 min. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH), followed by recrystallization from EtOH-water to give the title compound (47.7 mg) as an off-white solid.

후처리

  1. dry with materialunder dry atmosphere (CaCl2 tube) for 30 min
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water and brine successively
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane/EtOAc
  9. customEtOAc/MeOH), followed by recrystallization from EtOH-water

출처 및 근거

ORD 기록
ord-92d763b76399434696ae3c365334af20
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365540B2

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