Methanol → HCID 86629393, compound

HRID 244879Notes

Reaction equation

HRID 244879 reaction equation
[CH2:1]([N:5]1[C:17]2[C:16]3[CH:15]=[C:14]([CH:18]=C)[CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:20])[C:8]=2[N:7]=[CH:6]1)[CH:2]([CH3:4])[CH3:3].CSC.C[OH:25]>ClCCl>[NH2:20][C:9]1[C:8]2[N:7]=[CH:6][N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:17]=2[C:16]2[CH:15]=[C:14]([CH:18]=[O:25])[CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 21984387HCID 21984387, compound

Product 1

HCID 86629393HCID 86629393, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-isobutyl-8-vinyl-1H-imidazo[4,5-c]quinolin-4-amine (500 mg, 1.9 mmol) in dichloromethane (30 mL) and methanol (5 mL) was cooled to −78° C. Ozone was bubbled through the solution for 10 minutes. While still cold, the reaction was purged with oxygen for 15 minutes and dimethyl sulfide (0.7 mL, 9.4 mmol) was added. The reaction was warmed to ambient temperature and then concentrated under reduced pressure. The residue was dissolved in dichloromethane (50 mL) and washed with 1% aqueous sodium carbonate (2×15 mL). The combined aqueous fractions were extracted with chloroform (3×20 mL) and sequentially dried (MgSO4), filtered, and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a gradient of 0-6% methanol in dichloromethane) to provide 237 mg of 4-amino-1-isobutyl-1H-imidazo[4,5-c]quinoline-8-carbaldehyde as an off-white solid. MS (ESI) m/z 269 (M+H)+.

Workup

  1. customOzone was bubbled through the solution for 10 minutes
  2. customWhile still cold, the reaction was purged with oxygen for 15 minutes
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  5. washwashed with 1% aqueous sodium carbonate (2×15 mL)
  6. extractionThe combined aqueous fractions were extracted with chloroform (3×20 mL)
  7. dry with materialsequentially dried (MgSO4)
  8. filtrationfiltered
  9. custompurified by chromatography
  10. washeluting with a gradient of 0-6% methanol in dichloromethane)

Sources & evidence

ORD record
ord-82667745da694b06a642e1f3cbc8b124
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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