1,1,1-Triethoxybutane → 1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 547293

反応式

HRID 547293 の反応式
[C:1](OCC)(OCC)(OCC)[CH2:2][CH2:3][CH3:4].[CH3:14][S:15]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[CH:26][C:25]=1[NH2:34])(=[O:17])=[O:16].Cl.N1C=CC=CC=1>C(#N)C>[CH3:14][S:15]([CH2:18][CH2:19][O:20][CH2:21][CH2:22][N:23]1[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]=[C:1]1[CH2:2][CH2:3][CH3:4])(=[O:17])=[O:16]

参加物

5

反応物 3

HCID 3717791,1,1-TriethoxybutaneHCID 10176127Pyridinium chlorideHCID 86064731N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine

生成物 1

HCID 672039771-{2-[2-(methylsulfonyl)ethoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinoline収率 85.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Triethyl orthobutyrate (2.2 mL, 14 mmol) was added to a stirred solution of N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine (3.6 g, 12 mmol) in acetonitrile (60 mL). Pyridine hydrochloride (0.3 g) was added and the reaction mixture was heated to reflux with the volatiles being collected in a Dean Stark trap. After 40 minutes analysis by TLC indicated that the starting material was consumed. The reaction mixture was concentrated under reduced pressure to provide 3.7 g of 1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinoline as a white solid.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux with the volatiles
  3. custombeing collected in a Dean Stark trap
  4. customwas consumed
  5. concentrationThe reaction mixture was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-a8602f05cb754a1689b7a06ba4ceaf0b
出典データセット
uspto-grants-2011_05
特許番号
US07939526B2

関連ノート

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