反应详情

50 mg (0.139 mg) of 1-[3-(tert-butoxycarbonylamino)-propyl]-4-chloro-1H-imidazo[4,5-c]quinoline was dissolved in 3 ml of methylene chloride. 0.11 ml (1.39 mmol) of trifluoroacetic acid was added thereto and the mixture was stirred at room temperature for one day. The reaction mixture was concentrated under reduced pressure and 1 ml of a 1N sodium hydroxide aqueous solution and brine were added to the residue. The resulting solution was extracted with chloroform five times, thereafter the extract was dried (Na2SO4), and concentrated under reduced pressure. The residue was triturated with diethyl ether (containing a small amount of methylene chloride) and the precipitate thus formed was collected by filtration to obtain 14 mg (0.0536 mmol) of 1-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline shown below as white powder. ##STR37## Its spectroscopic data are as follows: IR (KBr) cm- 1 : 340, 1590, 1510. 1H-NMR (CDCl3 +CD3OD) 5 (ppm) : 2.06 (2H, m), 2.72 (2H, t, J=6.8 Hz), 2.98 (2H, b r), 4.64 (2H, t, J=7.0 Hz), 7.57 (1H, t, J=7.6 Hz), 7.61 (1H, t, J=7.6 Hz), 8.03 (1H, s), 8.05 (1H, d, J=8.0 Hz), 8.11 (1H, d, J=8.0 Hz).

1. concentrationThe reaction mixture was concentrated under reduced pressure and 1 ml of a 1N sodium hydroxide aqueous solution and brine
2. additionwere added to the residue
3. extractionThe resulting solution was extracted with chloroform five times
4. dry with materialthe extract was dried (Na2SO4)
5. concentrationconcentrated under reduced pressure
6. customThe residue was triturated with diethyl ether (
7. additioncontaining a small amount of methylene chloride) and the precipitate
8. customthus formed
9. filtrationwas collected by filtration