Hydrochloric Acid → HCID 68479389, compound

Participants

Reaction Conditions

Reaction Steps

To a 25 ml round bottom flask was added 8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-6-carbonitrile (0.62 g, 1.7 mmol) from (1a) and toluene (3.4 ml, 0.5 M) and the solution cooled to −5° C. To this was added dropwise, a 1.0 M solution of diisobutylaluminum hydride [DIBAL] in toluene (3.5 ml, 3.5 mmol) over a period of 10 minutes. The reaction was stirred at −5° C. for 1 hour and then warmed to room temperature and allowed to stir for an additional 2 hours. Dilute 1N HCl and ethyl acetate were added and the layers separated. The acidic aqueous layer was extracted 1 additional time with ethyl acetate and then basified with a 50% NaOH solution. The aqueous layer was extracted 2× with ethyl acetate and the combined organics were washed with brine (20 ml), dried over Na2SO4, filtered and concentrated in vacuo to provide crude 6-(aminomethyl)-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine (0.44 g) which was used as such in the subsequent step. m/z=(360, M+1).

Provenance & Evidence