Ethanol → HCID 57717506, compound

HRID 1984516Notes

Reaction equation

HRID 1984516 reaction equation
[NH2:1][C:2]1[C:11]2=[N:12][N:13]([CH2:21][CH2:22][O:23][CH3:24])[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:27])C.[OH-].[Na+].OO>O>[NH2:1][C:2]1[C:11]2=[N:12][N:13]([CH2:21][CH2:22][O:23][CH3:24])[C:14]([CH2:15][C:16]([CH3:20])([CH3:19])[C:17]([NH2:18])=[O:27])=[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 PeroxideHCID 14798Sodium HydroxideHCID 11965290HCID 11965290, compound

Product 1

HCID 57717506HCID 57717506, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

3-[4-Amino-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-2,2-dimethylpropanenitrile (436 mg, 1.35 mmol), ethanol (5 mL), sodium hydroxide (0.056 mL of 6 N), and 30% w/w hydrogen peroxide (0.54 mL, 4.7 mmol) were combined and heated at 50° C. for 18.5 hours. Water was added, and the ethanol was removed under reduced pressure. The mixture was extracted with chloroform, and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by IFC (silica cartridge) and recrystallized from 75% ethyl acetate in hexane. The crystals were washed with 50% ethyl acetate in hexane, dried on the vacuum filter funnel overnight, and further dried under vacuum at 9 Pa and 98° C. to provide 3-[4-amino-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-2,2-dimethylpropanamide as a white solid, mp 225-226° C.

Workup

  1. customthe ethanol was removed under reduced pressure
  2. extractionThe mixture was extracted with chloroform
  3. dry with materialthe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by IFC (silica cartridge)
  7. customrecrystallized from 75% ethyl acetate in hexane
  8. washThe crystals were washed with 50% ethyl acetate in hexane
  9. customdried on the vacuum
  10. filtrationfilter funnel overnight
  11. customfurther dried under vacuum at 9 Pa and 98° C.

Sources & evidence

ORD record
ord-5f152eb74a3c4bb591f6f7853872f615
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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