Hydrogen Peroxide → 2-(4-(7-chloro-1-(2,6-difluorophenyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-thienyl)acetamide

HRID 2206164Notes

Reaction equation

HRID 2206164 reaction equation
[Cl:1][C:2]1[C:3]2[N:11]([C:12]3[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=3[F:19])[N:10]=[C:9]([C:20]3[CH:21]=[C:22]([CH2:25][C:26]#[N:27])[S:23][CH:24]=3)[C:4]=2[C:5](=[O:8])[NH:6][CH:7]=1.C(=O)([O-])[O-:29].[K+].[K+].OO.O>CS(C)=O>[Cl:1][C:2]1[C:3]2[N:11]([C:12]3[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=3[F:19])[N:10]=[C:9]([C:20]3[CH:21]=[C:22]([CH2:25][C:26]([NH2:27])=[O:29])[S:23][CH:24]=3)[C:4]=2[C:5](=[O:8])[NH:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 137010632(4-(7-chloro-1-(2,6-difluorophenyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-thienyl)acetonitrile

Product 1

HCID 1370107392-(4-(7-chloro-1-(2,6-difluorophenyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-thienyl)acetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of (4-(7-chloro-1-(2,6-difluorophenyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)-2-thienyl)acetonitrile (69.4 mg) obtained in Example 152 and 2M aqueous potassium carbonate solution (0.431 mL) in DMSO (3 mL) was added 30% aqueous hydrogen peroxide (0.176 mL) under ice-cooling, and the reaction mixture was stirred at room temperature for 5 hr. The reaction mixture was allowed to be cooled to room temperature, water was added thereto under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained solid was washed with ethyl acetate and diisopropyl ether to give the title compound (55.8 mg).

Workup

  1. temperaturecooling
  2. temperatureto be cooled to room temperature
  3. temperatureunder ice-cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe obtained solid was washed with ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-b87192601a064c27ad2a6ab36ed28fa6
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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