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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
Notes
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Reaction equation

HRID 1043965 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 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
Yield 17.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d9e4dd86f0d6445e8d506b40fd0e6a2b
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563565B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes