Ethanol → HCID 57717531, compound

HRID 1984515Notes

Reaction equation

HRID 1984515 reaction equation
[NH2:1][C:2]1[C:11]2=[N:12][N:13]([CH2:21][CH2:22][CH3:23])[C:14]([CH2:15][C:16]([CH3:20])([CH3:19])[C:17]#[N:18])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.C([OH:26])C.[OH-].[NH4+].OO>O>[NH2:1][C:2]1[C:11]2=[N:12][N:13]([CH2:21][CH2:22][CH3:23])[C:14]([CH2:15][C:16]([CH3:19])([CH3:20])[C:17]([NH2:18])=[O:26])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen Peroxide2×HCID 14923Ammonium HydroxideHCID 11965289HCID 11965289, compound

Product 1

HCID 57717531HCID 57717531, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3-(4-Amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-2,2-dimethylpropanenitrile (657 mg, 2.14 mmol), ethanol (10 mL), concentrated ammonium hydroxide (2.1 mL), and 30% w/w hydrogen peroxide (2.8 g) were combined in a sealed glass tube and heated at 70° C. for seven hours. During this time, the reaction was periodically cooled and the pressure released. Additional hydrogen peroxide (1.4 g) was added, and the reaction was heated at 70° C. for five hours, with periodic cooling and venting. The reaction was cooled to 0° C., and water (25 mL) was added. A precipitate formed and was isolated by filtration, washed with water, purified by chromatography on a HORIZON HPFC instrument (40M cartridge), and recrystallized from acetonitrile. The crystals were dried on the vacuum filter funnel for two hours to provide 485 mg of 3-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-2,2-dimethylpropanamide as a white solid, mp 224-225° C.

Workup

  1. temperatureDuring this time, the reaction was periodically cooled
  2. temperaturethe reaction was heated at 70° C. for five hours
  3. temperaturewith periodic cooling
  4. temperatureThe reaction was cooled to 0° C.
  5. customA precipitate formed
  6. customwas isolated by filtration
  7. washwashed with water
  8. custompurified by chromatography on a HORIZON HPFC instrument (40M cartridge)
  9. customrecrystallized from acetonitrile
  10. customThe crystals were dried on the vacuum
  11. filtrationfilter funnel for two hours

Sources & evidence

ORD record
ord-0c955924891643b89ffa3f1b1fb8ada0
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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