Methanol → HCID 57657258, compound

HRID 244846Notes

Reaction equation

HRID 244846 reaction equation
CO.[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:22][O:23][CH3:24])[N:16]([CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][C:8]([CH:25]=[CH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:7][C:6]=2[N:5]=1>[Pd].C(O)C>[NH2:3][C:4]1[C:13]2[N:14]=[C:15]([CH2:22][O:23][CH3:24])[N:16]([CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][C:8]([CH2:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:7][C:6]=2[N:5]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 86629391HCID 86629391, compound

Product 1

HCID 57657258HCID 57657258, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A glass Parr vessel was charged with 10% palladium on carbon (200 mg), methanol (12.5 mL), ethanol (12.5 mL) and 1-{4-amino-2-(methoxymethyl)-7-[2-(methylsulfonyl)ethenyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (750 mg, 1.85 mmol). The vessel was evacuated and charged with hydrogen gas (40 psi, 2.8×105 Pa). The mixture was shaken at 50° C. for approximately 18 hours and then cooled to ambient temperature. The reaction mixture was sequentially filtered through a 0.2 micron PTFE membrane filter, concentrated under reduced pressure, and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 0-7% gradient of methanol in dichloromethane) to provide 195 mg of 1-{4-amino-2-(methoxymethyl)-7-[2-(methylsulfonyl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol as a white solid, mp 210-212° C.

Workup

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (40 psi, 2.8×105 Pa)
  3. temperaturecooled to ambient temperature
  4. filtrationThe reaction mixture was sequentially filtered through a 0.2 micron PTFE membrane
  5. filtrationfilter
  6. concentrationconcentrated under reduced pressure
  7. custompurified by chromatography
  8. washa HORIZON HPFC system (silica cartridge, eluting with 0-7% gradient of methanol in dichloromethane)

Sources & evidence

ORD record
ord-a889a040a2ec4676bf6ad91dd6137a62
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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