Tetrahydrofuran → HCID 178455216, Verbindung

HRID 388615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 388615
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Si:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[C:28]([Cl:36])[C:27]=1[NH2:37])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C1COCC1>N1C=CC=CC=1>[Si:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26]2[C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N:29]=[C:28]([Cl:36])[C:27]=2[N:37]=[C:1]1[OH:2])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 86633735HCID 86633735, Verbindung

Produkt 1

HCID 178455216HCID 178455216, VerbindungAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1,1′-Carbonyldiimidazole (32.6 g, 201 mmol) was added to a solution of N4-[4-(tert-butyldimethylsilanyloxy)butyl]-2-chloroquinoline-3,4-diamine (50.96 g, 134.1 mmol), THF (250 mL), and pyridine (250 mL), and the reaction was heated at 80° C. overnight and allowed to cool. The volatiles were removed under reduced pressure. The residue was dissolved in ethyl acetate (600 mL), and the resulting solution was washed sequentially with brine (2×400 mL) and water (2×400 mL) and then concentrated under reduced pressure. The resulting solid was triturated with diethyl ether (1 L), collected by filtration, washed with diethyl ether (800 mL), and dried under vacuum for 30 minutes to provide 28.39 g of 1-[4-(tert-butyldimethylsilanyloxy)butyl]-4-chloro-1H-imidazo[4,5-c]quinolin-2-ol as a white solid.

Aufarbeitung

  1. temperatureto cool
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (600 mL)
  4. washthe resulting solution was washed sequentially with brine (2×400 mL) and water (2×400 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid was triturated with diethyl ether (1 L)
  7. filtrationcollected by filtration
  8. washwashed with diethyl ether (800 mL)
  9. customdried under vacuum for 30 minutes

Quellen und Nachweise

ORD-Eintrag
ord-1e035d8b6e774ea1926dd07963d1f8d3
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377957B2

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