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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
ノート
印刷プレビュー

反応式

HRID 1043965 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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)-one収率 17.4%

試薬・触媒・溶媒

2
HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d9e4dd86f0d6445e8d506b40fd0e6a2b
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08563565B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート