1-{4-amino-7-[2-(methylsulfonyl)ethenyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol → 1-{4-amino-7-[2-(methylsulfonyl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol

HRID 244835Notes

Reaction equation

HRID 244835 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH:20]=[CH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:5][C:4]=2[N:3]=1>[Pd].CO>[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][C:16]([CH3:17])([OH:18])[CH3:19])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 866293901-{4-amino-7-[2-(methylsulfonyl)ethenyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol

Product 1

HCID 576572611-{4-amino-7-[2-(methylsulfonyl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-olYield 46.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A glass Parr vessel was charged with 10% palladium on carbon (0.1 g), methanol (50 mL) and 1-{4-amino-7-[2-(methylsulfonyl)ethenyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol (380 mg, 1.05 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. The reaction was cooled to ambient temperature, filtered, and then concentrated under reduced pressure. The resulting crude product was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-35% gradient of CMA in chloroform) followed by recrystallization from acetonitrile to provide 176 mg of 1-{4-amino-7-[2-(methylsulfonyl)ethyl]-1H-imidazo[4,5-c]quinolin-1-yl}-2-methylpropan-2-ol as an off-white solid, mp 269-271° C.

Workup

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (40 psi, 2.8×105 Pa)
  3. temperatureThe reaction was cooled to ambient temperature
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude product was purified by chromatography
  7. washeluting with a 0-35% gradient of CMA in chloroform)
  8. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-b32d7b9de6254ad39e53876d111ca6c2
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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