1-[3-(benzyloxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline → 1-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline.acetate
Reaction equation
Br.[C:2]([OH:5])(=[O:4])[CH3:3].C(OC([NH:16][CH2:17][CH2:18][CH2:19][N:20]1[C:32]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[C:24]([Cl:33])[C:23]=2[N:22]=[CH:21]1)=O)C1C=CC=CC=1>>[NH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:32]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[C:24]([Cl:33])[C:23]=2[N:22]=[CH:21]1.[C:2]([O-:5])(=[O:4])[CH3:3]Participants
3
Procedure
3 ml of 33% hydrogen bromide-acetic acid was added to 0.12 g (0.304 mmol) of 1-[3-(benzyloxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline and the mixture was stirred at room tempterature for 1.5 hours. After the reaction mixture was concentrated under reduced pressure, a 1N sodium hydroxide aqueous solution and brine were added to the residue and the solution was extracted five times with chloroform. The organic phase was dried (Na2SO4), the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol:32% acetic acid=12:6:1 (v/v)) to obtain 60 mg (0.187 mmol) of 1-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline·acetate shown below as a pale yellow solid. ##STR32## Its spectroscopic data are as follows: 1H-NMR (CD3OD) δ (ppm): 1.94 (3H, s), 2.39 (2H, m), 3.12 (2H, t, J=7.8 Hz), 4.82 (2H, t, J=7.2 Hz), 7.70 (2H, m), 7.97 (1H, d, J=8.0 Hz), 8.27 (1H, d, J=8.0 Hz), 8.41 (1H, s).