反应详情

温度

0 °C

A solution of 1-(2-aminoethoxy)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (30 mg, 0.10 mmol) and succinimido 3-(triphenylmethylthio)propanoate (54 mg, 0.12 mmol) in dichloromethane (1 mL) was stirred for 24 hours at room temperature. Methanol (1 mL) was added and stirring was continued for another 5 days. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane (2 mL) and triethylsilane (0.16 mL) and cooled to 0° C. Trifluoroacetic acid (0.4 mL) was added. The solution was stirred for 30 min; then it was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (gradient elution with a solution of 2% ammonium hydroxide in methanol and chloroform) to provide 18.2 mg of N-(2-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]oxy}ethyl)-3-mercaptopropanamide as a solid. HRMS (ESI) calcd for C18H24N5O3S+H 390.1600, found 390.1579.

1. filtrationThe mixture was filtered
2. concentrationthe filtrate was concentrated
3. dissolutionThe residue was dissolved in dichloromethane (2 mL)
4. additionTrifluoroacetic acid (0.4 mL) was added
5. stirringThe solution was stirred for 30 min
6. concentrationthen it was concentrated under reduced pressure
7. customThe crude product was purified by flash chromatography on silica gel (
8. washgradient elution with a solution of 2% ammonium hydroxide in methanol and chloroform)