Hydrogen Peroxide → HCID 178437860, compound

HRID 487258Notes

Reaction equation

HRID 487258 reaction equation
[CH:1]1([N:6]2[C:10]([NH:11][C:12]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=[CH:16][CH:15]=3)=O)=[C:9]([C:24]#[N:25])[C:8]([CH2:26][CH3:27])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:28].[K+].O.OO>C(O)(=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:14]4[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[N:17]=[CH:16][CH:15]=4)=[N:25][C:24](=[O:28])[C:9]3=[C:8]([CH2:26][CH3:27])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide3×HCID 962WaterHCID 14797Potassium Hydroxide3×HCID 194328031-cyclopentyl-3-ethyl-4-cyano-5-(4-quinolinecarboxamido)-1H-pyrazole

Product 1

HCID 178437860HCID 178437860, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 1-cyclopentyl-3-ethyl-4-cyano-5-(4-quinolinecarboxamido)-1H-pyrazole (4.6 g, 12.7 mmol), potassium hydroxide (1.7 g, 25.4 mmol) and water (250 ml) at room temperature was added 30% hydrogen peroxide (7.8 ml, 76.0 mmol). The reaction mixture was heated to reflux and stirred for 24 hours. One equivalent of potassium hydroxide and 2 equivalents of 30% hydrogen peroxide were added and the mixture was refluxed for another 24 hours. One equivalent of potassium hydroxide and 2 equivalents of 30% hydrogen peroxide were again added and the mixture was heated at reflux for 3 days. The reaction mixture was cooled to room temperature, treated with acetic acid until a pH of 6.5 was obtained and the resulting precipitate was collected by filtration. The product was purified by column chromatography on silica eluting with ethyl acetate to afford 1.3 g (35%) of 1-cyclopentyl-3-ethyl-6-(4-quinolinyl)-pyrazolo[3,4-d]pyrimidin-4-one as a white solid, m.p. 205°-206° C., when recrystallized from ethyl acetate and dried at 110° C. for 16 hours in high vacuum.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturethe mixture was refluxed for another 24 hours
  4. temperaturethe mixture was heated
  5. temperatureat reflux for 3 days
  6. customwas obtained
  7. filtrationthe resulting precipitate was collected by filtration
  8. customThe product was purified by column chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-fa2e3d81e8834fcdac6d8fee9b5ec5a6
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

Loading…