Water → HCID 67204871, compound

HRID 547309Notes

Reaction equation

HRID 547309 reaction equation
[H-].[Na+].[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:20][C:21]2([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH3:4].[CH:27]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH2:28].O>O1CCCC1>[CH2:3]([O:5][CH2:6][C:7]1[N:8]([CH2:20][C:21]2([O:26][CH2:28][CH2:27][S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 19354Methyl vinyl sulfone2×HCID 24758Sodium hydrideHCID 57515382HCID 57515382, compound

Product 1

HCID 67204871HCID 67204871, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil, 36 mg, 0.8 mmol) was added to a stirred solution of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclopentanol (1.45 g, 4.50 mmol) and methyl vinyl sulfone (0.95 g, 8.9 mmol) in tetrahydrofuran (18 mL). The reaction mixture was stirred at room temperature for 1 hour and additional methyl vinyl sulfone (0.47 g) was added. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford an oil that was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to provide 1.2 g of 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclopentyl}methyl)-1H-imidazo[4,5-c]quinoline as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford an oil that
  7. customwas purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-495214635ddb4d36a448b61859c7cee0
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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