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

HRID 547293

Reaktionsgleichung

Reaktionsgleichung von HRID 547293
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 672039771-{2-[2-(methylsulfonyl)ethoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinolineAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a8602f05cb754a1689b7a06ba4ceaf0b
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939526B2

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