Reaktion #479224

Reaktionsgleichung

5-Dimethylamino-1-naphthalenesulfonyl chloride

N,N-diisopropylethylamine

dichloromethane

1-(4-aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

→

N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(dimethylamino)-1-naphthalenesulfonamide

Ausbeute 71.5%

Lösungsmittel

Methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas obtained
2. 2
   workup.ADDITIONSilica gel was added to the reaction mixture
3. 3
   Sonstigethe solvents were removed
4. 4
   Wascheneluted with chloroform in a stepwise gradient to 9:1 chloroform
5. 5
   SonstigeThe resulting product was recrystallized from N,N-dimethylformamide

Vorschrift

5-Dimethylamino-1-naphthalenesulfonyl chloride (1.82 g, 6.74 mmol) was added to a mixture of N,N-diisopropylethylamine (1.23 mL, 7.06 mmol), dichloromethane (15 mL) and 1-(4-aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine (2.0 g, 6.42 mmol). The reaction mixture was allowed to stir at ambient temperature overnight. Methanol was added to the reaction mixture until a clear solution was obtained. Silica gel was added to the reaction mixture and then the solvents were removed. The silica gel was placed in a column and then eluted with chloroform in a stepwise gradient to 9:1 chloroform:methanol. The resulting product was recrystallized from N,N-dimethylformamide and deionized water to provide 2.5 g of N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-5-(dimethylamino)-1-naphthalenesulfonamide as a yellow crystalline solid, m.p. 223-224° C. Analysis: Calculated for C30H36N6O2S: % C, 66.15; % H, 6.66;% N, 15.43; Found: % C, 66.36; % H, 6.34; % N, 15.23.

Quelle