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Acetic Acid → (S)-8-fluoro-7-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one

HRID 1043965
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HRID 1043965 반응식
[OH-].[Na+].F[C:4]1[CH:9]=[C:8]([C:10]2[C:11]([O:18][CH3:19])=[N:12][C:13]([CH3:17])=[CH:14][C:15]=2[CH3:16])[C:7]([F:20])=[CH:6][C:5]=1[C:21]1[N:25]([C@H:26]2[CH2:30][CH2:29][O:28][CH2:27]2)[N:24]=[CH:23][C:22]=1[C:31]([NH2:33])=[O:32].O.C(O)(=O)C>CS(C)=O.C(OCC)(=O)C>[F:20][C:7]1[C:8]([C:10]2[C:11]([O:18][CH3:19])=[N:12][C:13]([CH3:17])=[CH:14][C:15]=2[CH3:16])=[CH:9][C:4]2[NH:33][C:31](=[O:32])[C:22]3[CH:23]=[N:24][N:25]([C@H:26]4[CH2:30][CH2:29][O:28][CH2:27]4)[C:21]=3[C:5]=2[CH:6]=1
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참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 866864005-(2,5-difluoro-4-(2-methoxy-4,6-dimethylpyridin-3-yl)phenyl)-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxamide

생성물 1

HCID 136253994(S)-8-fluoro-7-(2-methoxy-4,6-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one수율 17.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
75 °C

실험 절차

Sodium hydroxide (powder, 74 mg) was added to a solution of 5-(2,5-difluoro-4-(2-methoxy-4,6-dimethylpyridin-3-yl)phenyl)-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxamide (199 mg) in DMSO (2 mL), and the reaction mixture was stirred at 75° C. for 1.5 hours. After the reaction mixture was cooled to room temperature, water, acetic acid (0.106 mL) and ethyl acetate were added to the reaction mixture with stirring. After the precipitated solid was filtered, organic layer was washed with water, a saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and the desiccant was removed by filtration. After the filtrate was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 55% to 90% to 96%), and the resulting crude was solidified by adding n-heptane/MTBE to give the title compound (33 mg).

후처리

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. stirringwith stirring
  3. filtrationAfter the precipitated solid was filtered
  4. washorganic layer was washed with water
  5. dry with materiala saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate
  6. customthe desiccant was removed by filtration
  7. concentrationAfter the filtrate was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 55% to 90% to 96%)
  9. additionby adding n-heptane/MTBE

출처 및 근거

ORD 기록
ord-d9e4dd86f0d6445e8d506b40fd0e6a2b
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08563565B2

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