Hydrogen Peroxide → HCID 57657254, compound

HRID 244875Notes

Reaction equation

HRID 244875 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH3:23])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:24][CH2:25][C:26]#[N:27])=[CH:5][C:4]=2[N:3]=1.[OH-:28].[Na+].OO>CO>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH3:23])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:24][CH2:25][C:26]([NH2:27])=[O:28])=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 57657250HCID 57657250, compound

Product 1

HCID 57657254HCID 57657254, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

3-[4-Amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanenitrile (590 mg, 1.6 mmol), 10% aqueous sodium hydroxide (132 mg, 0.33 mmol), and 30% aqueous hydrogen peroxide (516 mg, 4.55 mmol) were combined in methanol (75 mL) and the reaction was heated at 50° C. for 18 hours. The mixture was concentrated under reduced pressure and then partitioned between chloroform (75 mL) and water (75 mL). The fractions were separated and the aqueous fraction was extracted with chloroform (3×25 mL). The combined organic fractions were sequentially dried (MgSO4), filtered, concentrated to dryness and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 2 L of 10% methanol in dichloromethane). A final recrystallization from acetonitrile provided 35 mg of 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanamide as an off-white solid, mp 197-199° C.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompartitioned between chloroform (75 mL) and water (75 mL)
  3. customThe fractions were separated
  4. extractionthe aqueous fraction was extracted with chloroform (3×25 mL)
  5. dry with materialThe combined organic fractions were sequentially dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. custompurified by chromatography
  9. washa HORIZON HPFC system (silica cartridge, eluting with 2 L of 10% methanol in dichloromethane)
  10. customA final recrystallization from acetonitrile

Sources & evidence

ORD record
ord-a1ffc210a9e5487ebf739b9f84ec988a
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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