Formamide → Imiquimod

HRID 425254

Reaktionsgleichung

Reaktionsgleichung von HRID 425254
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[CH:7]([NH2:9])=O.ClC1[C:20]2[N:21]=[CH:22][NH:23][C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1>CC(N(C)C)=O>[CH2:1]([N:23]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[C:7]([NH2:9])[C:20]=2[N:21]=[CH:22]1)[CH:2]([CH3:5])[CH3:3]

Komponenten

5

Edukt 3

HCID 713FormamideHCID 23665647Potassium tert-butoxideHCID 178478309HCID 178478309, Verbindung

Produkt 1

HCID 57469ImiquimodAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Potassium tert-butoxide (4.32 g, 0.038 mole), 4.5 mL of dimethylacetamide and 1.53 mL (0.038 mole) of formamide were added in a 50-mL round-bottomed flask, under inert atmosphere followed by stirring for 30 minutes. After addition of 4-chloro-1H-imidazo[4,5-c]quinoline (1 g, 3.8 mmoles), the mixture was heated at 120° C., followed by stirring for 1 hour and then cooled to room temperature. The reaction mixture was filtered followed by washing with abundant water and dried to give 0.4 g of 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine. Yield 39%.

Aufarbeitung

  1. stirringby stirring for 1 hour
  2. temperaturecooled to room temperature
  3. filtrationThe reaction mixture was filtered
  4. washby washing with abundant water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2267e79c7f254fefbc3f9dc880e10ec7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106202B2

Verknüpfte Notizen

Wird geladen…