Trichloroacetyl isocyanate → 8-benzyloxy-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 598313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 598313
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N+:15]([O-])=[CH:14][C:13]3[N:20]=[CH:21][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C([N:31]=C=O)=O.C[O-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14]([NH2:31])[C:13]3[N:20]=[CH:21][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 76400Trichloroacetyl isocyanate2×HCID 10942334Sodium MethoxideHCID 670510288-benzyloxy-1-(2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinoline

Produkt 1

HCID 575453368-benzyloxy-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Versuchsvorschrift

A modification of the general method described in Part C of Example 3 was followed using 8-benzyloxy-1-(2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinoline (2.0 g, 5.8 mmol) as the starting material. The reaction with trichloroacetyl isocyanate was not complete after one hour as evidenced by a TLC analysis. Additional trichloroacetyl isocyanate (0.1 equivalent) was added, and the reaction was stirred for an additional hour. Following the reaction with sodium methoxide, the solid product was isolated by filtration and recrystallized from ethanol. The crystals were dried overnight in a vacuum oven at 45° C. to provide 1.6 g of 8-benzyloxy-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 214-216° C.

Aufarbeitung

  1. customthe solid product was isolated by filtration
  2. customrecrystallized from ethanol
  3. customThe crystals were dried overnight in a vacuum oven at 45° C.

Quellen und Nachweise

ORD-Eintrag
ord-3cfa001d4cf34e69ad763c79617cc9ec
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897597B2

Notizen zur Reaktion

Wird geladen…