Imiquimod → 8-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9448

Reaktionsgleichung

Reaktionsgleichung von HRID 9448
[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:19][C:13]1[CH:12]=[CH:11][C:10]2[N:9]=[C:8]([NH2:17])[C:7]3[N:6]=[CH:5][N:4]([CH2:3][CH:2]([CH3:18])[CH3:1])[C:16]=3[C:15]=2[CH:14]=1

Komponenten

4

Edukt 2

HCID 57469ImiquimodHCID 67184N-bromobutanimide

Produkt 1

HCID 111745978-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amineAusbeute 22,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (30.0 g, 125 mmol) in chloroform (620 mL) was heated to 50° C., and N-bromosuccinimide (28.8 g, 162 mmol) was added in five portions over a period of five minutes. The resulting dark red solution was heated at reflux for 45 minutes, allowed to cool to ambient temperature, and stirred for one hour. A precipitate formed, was isolated by filtration, and was washed with water and diethyl ether to provide 9.0 g of 8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinolin-4-amine as a solid.

Aufarbeitung

  1. temperatureThe resulting dark red solution was heated
  2. temperatureat reflux for 45 minutes
  3. customA precipitate formed
  4. customwas isolated by filtration
  5. washwas washed with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a0aab8bc0b124b31a57accf5057cc740
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091214B2

Verknüpfte Notizen

Wird geladen…