Pyridinium chloride → 2-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline

HRID 432847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432847
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[CH:11][C:10]=1[NH:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl.N1C=CC=CC=1>N1C=CC=CC=1>[CH2:21]([C:20]1[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][S:2][CH3:1])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:19]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

4

Edukt 2

HCID 10176127Pyridinium chlorideHCID 22320422N-(4-[{5-(methylthio)pentyl]amino}quinolin-3-yl)heptanamide

Produkt 1

HCID 223205532-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinolineAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A round bottom flask was charged with a magnetic stir bar, N-(4-{[-(methylthio)pentyl]amino}quinolin-3-yl)heptanamide (4.44 g, 11.46 mmol), pyridine hydrochloride (0.13 g, 1.15 mmol), and anhydrous pyridine (50 mL) under a nitrogen atmosphere. The reaction was judged to be complete after stirring at reflux for 1.5 hours. The solution was cooled and partitioned between ethyl acetate and water. The layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford 2-hexyl-1-[5-(methylthio)pentyl]-1H-imidazo[4,5-c]quinoline (4.0 g, 10.82 mmol) as a brown oil which was used without further purification.

Aufarbeitung

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. temperatureat reflux for 1.5 hours
  3. temperatureThe solution was cooled
  4. custompartitioned between ethyl acetate and water
  5. customThe layers were separated
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4db48f60f54e477a9ce26693f75cff51
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664264B2

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