Water → HCID 86613464, compound

HRID 547303Notes

Reaction equation

HRID 547303 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:13]2[N:14]=[C:15]([CH3:22])[N:16]([CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1.[CH:23]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH2:24].O>O1CCCC1>[Cl:3][C:4]1[C:13]2[N:14]=[C:15]([CH3:22])[N:16]([CH2:17][C:18]([CH3:19])([O:20][CH2:24][CH2:23][S:25]([CH3:28])(=[O:27])=[O:26])[CH3:21])[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 19737317HCID 19737317, compound

Product 1

HCID 86613464HCID 86613464, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 41 mg, 1.04 mmol) was added to a stirred solution of 1-(4-chloro-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (prepared as described in U.S. Pat. No. 5,266,575 Comparative Example C1, 3.00 g, 10.4 mmol) and methyl vinyl sulfone (2.20 g, 20.7 mmol) in tetrahydrofuran (41 mL). The reaction mixture was stirred at room temperature for 17 hours. Water (100 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 ethyl acetate) to yield 1.8 g of 4-chloro-2-methyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline as a white solid.

Workup

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

Sources & evidence

ORD record
ord-135819eec56b465e833af8a6b99419d1
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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