Hydrogen Peroxide → HCID 57657242, compound

HRID 244856Notes

Reaction equation

HRID 244856 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH3:22])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:23][CH2:24][C:25]#[N:26])=[CH:5][C:4]=2[N:3]=1.[OH-:27].[Na+].OO>CO>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH3:22])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:23][CH2:24][C:25]([NH2:26])=[O:27])=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 57657236HCID 57657236, compound

Product 1

HCID 57657242HCID 57657242, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[4-Amino-1-(2-hydroxy-2-methylpropyl)-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanenitrile (430 mg, 1.30 mmol) in methanol (75 mL) was heated to 50° C. in an oil bath. Aqueous 10% sodium hydroxide (0.33 mmol) and 30% aqueous hydrogen peroxide (516 mg, 4.55 mmol) were added and the reaction was stirred for 18 hours. The mixture was cooled to ambient temperature and then concentrated under reduced pressure. The resulting solid was slurried in water (70 mL). The aqueous mixture was washed with chloroform (35 mL), concentrated to a wet solid, slurried in methanol (100 mL) and filtered. The filtrate was absorbed onto silica (1 tbsp) and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with CMA:chloroform gradient; 0-20% CMA over 1400 mL, followed by 20-25% CMA over 1200 mL). The material was further purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-9% gradient of methanol in dichloromethane) to provide 102 mg of 3-[4-amino-1-(2-hydroxy-2-methylpropyl)-2-(methoxymethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanamide as a white solid, mp 228-230° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe aqueous mixture was washed with chloroform (35 mL)
  3. concentrationconcentrated to a wet solid, slurried in methanol (100 mL)
  4. filtrationfiltered
  5. customThe filtrate was absorbed onto silica (1 tbsp)
  6. custompurified by chromatography
  7. washa HORIZON HPFC system (silica cartridge, eluting with CMA:chloroform gradient; 0-20% CMA over 1400 mL, followed by 20-25% CMA over 1200 mL)
  8. customThe material was further purified by chromatography
  9. washeluting with a 0-9% gradient of methanol in dichloromethane)

Sources & evidence

ORD record
ord-74bbf4be50724918a09052650550b9e1
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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