Methanol → 1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 244873Notes

Reaction equation

HRID 244873 reaction equation
CO.C([C:5]1[N:6]([CH2:25][CH:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:7]2[C:16]3[CH:15]=[CH:14][C:13](C=CS(C)(=O)=O)=[CH:12][C:11]=3[N:10]=[C:9]([NH2:23])[C:8]=2[N:24]=1)C>[Pd].C(O)C>[O:29]1[CH2:30][CH2:31][CH:26]([CH2:25][N:6]2[C:7]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=[C:9]([NH2:23])[C:8]=3[N:24]=[CH:5]2)[CH2:27][CH2:28]1

Participants

5

Reactant 2

HCID 887MethanolHCID 866293922-ethyl-7-[2-(methylsulfonyl)ethenyl]-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 1317312061-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A glass Parr vessel was charged with 10% palladium on carbon (0.2 g), methanol (25 mL), ethanol (25 mL) and 2-ethyl-7-[2-(methylsulfonyl)ethenyl]-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine (315 mg, 0.76 mmol). The vessel was evacuated and charged with hydrogen gas (40 psi, 2.8×105 Pa). The reaction was shaken at 50° C. for approximately 18 hours and then cooled to ambient temperature. The reaction mixture was sequentially filtered, concentrated under reduced pressure, and purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with CMA:chloroform gradient, 0-10% CMA over 1000 mL followed by 10-25% CMA over 1000 mL). A final recrystallization from acetonitrile provided 125 mg of 2-ethyl-7-[2-(methylsulfonyl)ethyl])-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white crystalline solid, mp 246.5-249.0° 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
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography
  7. washa HORIZON HPFC system (silica cartridge, eluting with CMA:chloroform gradient, 0-10% CMA over 1000 mL followed by 10-25% CMA over 1000 mL)
  8. customA final recrystallization from acetonitrile

Sources & evidence

ORD record
ord-bc16f9b6cb3b418c9e6439bacc98e01f
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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