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

HRID 547317
ノート
印刷プレビュー

反応式

HRID 547317 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8e82a50220e8444ebf8602b624123ac2
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07939526B2

反応ノート

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