Hydrogen Peroxide → HCID 178433701, compound

HRID 1736552Notes

Reaction equation

HRID 1736552 reaction equation
[OH-:1].[K+].[CH:3]1([N:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[CH:18][CH:19]=[C:20]4[C:25]=3[N:24]=[CH:23][CH:22]=[CH:21]4)=O)=[C:11]([C:26]#[N:27])[C:10]([CH3:28])=[N:9]2)[CH2:7][CH2:6][CH2:5][CH2:4]1.OO>O.CO>[CH:3]1([N:8]2[C:12]3=[N:13][C:14]([C:16]4[CH:17]=[CH:18][CH:19]=[C:20]5[C:25]=4[N:24]=[CH:23][CH:22]=[CH:21]5)=[N:27][C:26](=[O:1])[C:11]3=[C:10]([CH3:28])[NH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 14797Potassium Hydroxide2×HCID 19432799N-(4-Cyano-1-cyclopentyl-3-methyl-1H-pyrazol-5-yl)-8-quinolinecarboxamide

Product 1

HCID 178433701HCID 178433701, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To potassium hydroxide (0.2 g, 3.0 mmol) in water (75 ml) cooled in an ice bath was added 1-cyclopentyl-3-methyl-4-cyano-5-(8-quinolinecarboxamido)-1H-pyrazole (2.05 g, 5.9 mmol) in methanol (30 ml) followed by 30% hydrogen peroxide (3.0 ml, 30 mmol). The reaction mixture was slowly warmed to room temperature and then refluxed for 24 hours. Additional potassium hydroxide (3.0 mmol) and 30% hydrogen peroxide (30 mmol) were added and the reaction mixture was refluxed for 1.5 hours. The reaction mixture was cooled in an ice-bath, the precipitated product was collected by filtration through a glass frit and was washed with water, then ether. Recrystallization from ethyl acetate afforded 0.2 g (10%) of 1-cyclopentyl-3-methyl-6-(8-quinolinyl)-pyrazolo[3,4-d]pyrimidin-4-one as yellow crystals, m.p.242°-244° C. when dried for 24 hours at 120° C. in high vacuum.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperaturethe reaction mixture was refluxed for 1.5 hours
  3. temperatureThe reaction mixture was cooled in an ice-bath
  4. filtrationthe precipitated product was collected by filtration through a glass frit
  5. washwas washed with water
  6. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-f61a561fdf9f42ce9c97d283c8e8dc07
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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