Ethanol → HCID 57545294, compound

HRID 2383171Notes

Reaction equation

HRID 2383171 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][O:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-])=O)[CH:27]=3)=[CH:5][C:4]=2[N:3]=1.C(O)C>[Pt].CO>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][O:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:17])([OH:18])[CH3:19])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([NH2:32])[CH:27]=3)=[CH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 57545339HCID 57545339, compound

Product 1

HCID 57545294HCID 57545294, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst2×HCID 887MethanolSolvent

Procedure

1-[4-Amino-2-(2-methoxyethyl)-7-(3-nitrobenzyloxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol (3.1 g, 6.66 mmol) was mixed with 100 mL of warm ethanol and 1 g of 5% platinum on carbon. The mixture was shaken under hydrogen pressure (50 psi, 3.4×105 pa) for 5 hours. The material had come out of solution so an additional 100 mL of methanol and 0.5 g platinum catalyst were added. After shaking under hydrogen pressure overnight, the mixture was filtered through CELITE filter agent. The filter cake was washed with 3×75 mL portions of hot methanol and the filtrates were combined and concentrated under reduced pressure. An orange foam resulted which was purified by column chromatography using silica gel. The polar component of the eluent was chloroform:methanol:2% aqueous ammonium hydroxide 80:18:2 (CMA), and elution was carried out with CMA:chloroform in a gradient from 0:100 to 40:60. Fractions containing product were combined and concentrated to yield 1.55 g of 1-[4-amino-7-(3-aminobenzyloxy)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off-white solid. A small portion was recrystallized from acetonitrile to provide an analytical sample, mp 203.0-206.0° C.

Workup

  1. additionwere added
  2. stirringAfter shaking under hydrogen pressure overnight
  3. filtrationthe mixture was filtered through CELITE
  4. filtrationfilter agent
  5. washThe filter cake was washed with 3×75 mL portions of hot methanol
  6. concentrationconcentrated under reduced pressure
  7. customAn orange foam resulted which
  8. customwas purified by column chromatography
  9. washmethanol:2% aqueous ammonium hydroxide 80:18:2 (CMA), and elution
  10. additionFractions containing product
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-048b4da16ed64a69996b38dd203cee0f
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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