Benzylamine → 4-benzylamino-1-[3-(tert-butoxycarbonylamino)propyl]-1H-imidazo[4,5-c]quinoline

Participants

Reaction Conditions

Reaction Steps

One ml of benzylamine was added to 30 mg (0.0831 mmol) of 1-[3-(tert-butoxycarbonylamino)propyl]-4-chloro-1H-imidazo[4,5-c]quinoline and the mixture was stirred at 150° C. for 3 hours. Excess benzylamine was distilled off under reduced pressure and 1N hydrochloric acid and brine were added thereto. The mixture was extracted twice with methylene chloride. The organic phase was washed with a saturated sodium hydrogencarbonate aqueous solution and dried (Na2SO4). The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=150:1 (v/v)) to obtain 35 mg (0.0811 mmol) of 4-benzylamino-1-[3-(tert-butoxycarbonylamino)propyl]-1H-imidazo[4,5-c]quinoline shown below as white powder (mp: 171-172.5° C.). ##STR39## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3330, 1700, 1590, 1540. 1H-NMR (CDCl3) δ (ppm) :1.46 (9H, s), 2.18 (2H, m), 3.25 (2H, m), 4.57 (2H, t, J=7.0 Hz), 4.64 (1H, br), 4.95 (2H, d, J=5.2 Hz), 6.05 (1H, br), 7.26~7.36 (4H, m), 7.47 (2H, d, J=7.6 Hz), 7.51 (1H, t, J=7.6 Hz), 7.82 (1H, s), 7.92 (2H, t, J=8.0 Hz).

Provenance & Evidence