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Methyl vinyl sulfone → 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-1H-imidazo[4,5-c]quinoline

HRID 547317
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HRID 547317 반응식
N12CCCN=C1CCCCC2.[CH:12]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH2:13].[CH2:18]([O:20][CH2:21][C:22]1[N:23]([CH2:35][C:36]2([OH:40])[CH2:39][CH2:38][CH2:37]2)[C:24]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:34]=1)[CH3:19].[H-].[Na+]>O1CCCC1.O>[CH2:18]([O:20][CH2:21][C:22]1[N:23]([CH2:35][C:36]2([O:40][CH2:13][CH2:12][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:39][CH2:38][CH2:37]2)[C:24]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[CH:26][C:25]=2[N:34]=1)[CH3:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 575153931-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclobutanol

생성물 1

HCID 672036362-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-1H-imidazo[4,5-c]quinoline수율 64.8%

시약·촉매·용매 2

HCID 962Water용매
HCID 8028Tetrahydrofuran용매

실험 절차

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.10 mL, 0.74 mmol) followed by methyl vinyl sulfone (1.60 g, 14.8 mmol) were added to a stirred solution of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclobutanol (2.30 g, 7.39 mmol) in tetrahydrofuran (30 mL). The reaction mixture was stirred at room temperature for 1 hour and a small amount of sodium hydride (60% dispersion in mineral oil) 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 2.0 g of 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-1H-imidazo[4,5-c]quinoline as an oil.

후처리

  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)

출처 및 근거

ORD 기록
ord-8e82a50220e8444ebf8602b624123ac2
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07939526B2

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