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Water → 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclohexyl}methyl)-1H-imidazo[4,5-c]quinoline

HRID 547311
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 547311
[H-].[Na+].[CH:3]([S:5]([CH3:8])(=[O:7])=[O:6])=[CH2:4].[CH2:9]([O:11][CH2:12][C:13]1[N:14]([CH2:26][C:27]2([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:25]=1)[CH3:10].O>O1CCCC1>[CH2:9]([O:11][CH2:12][C:13]1[N:14]([CH2:26][C:27]2([O:33][CH2:4][CH2:3][S:5]([CH3:8])(=[O:7])=[O:6])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:25]=1)[CH3:10]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 19354Methyl vinyl sulfone2×HCID 24758Sodium hydride2×HCID 575153771-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanol

Produkt 1

HCID 672040532-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclohexyl}methyl)-1H-imidazo[4,5-c]quinolineAusbeute 16,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion in oil, 25 mg, 0.62 mmol) followed by methyl vinyl sulfone (1.30 g, 12.4 mmol) were added to a stirred solution of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanol (2.1 g, 6.2 mmol) in tetrahydrofuran (25 mL). The reaction mixture was heated at reflux for 2 hours and additional methyl vinyl sulfone (1 equivalent) and sodium hydride (60% dispersion in oil, spatula tip full) were added. The mixture was allowed to stir overnight at room temperature. Water (50 mL) was added and a precipitate formed that was removed by filtration. The filtrate was extracted with dichloromethane (2×50 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 0.45 g of 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclohexyl}methyl)-1H-imidazo[4,5-c]quinoline as a colorless oil.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. customa precipitate formed
  4. customthat was removed by filtration
  5. extractionThe filtrate was extracted with dichloromethane (2×50 mL)
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford an oil that
  11. customwas purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0de65d8d51ea4c5d800cdecc4dfd9295
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07939526B2

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