Hydrochloric Acid → HCID 86656329, compound

Participants

Reaction Steps

Crude ethyl 4-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-6-chloro-1,5-naphthyridine-3-carboxylate (54) (240.8 g, 554 mmol) was suspended in a 1:1:1 mixture of MeOH:THF:H2O (500 mL each) and LiOH (39.8 g, 1.66 mol, 3 eq) was added. The mixture was maintained at rt and monitored by LCMS. After consumption of starting material, the volatiles were removed under vacuum and the resultant solution was neutralized by the addition of 6N HCl (˜3 eq). The mixture was then carefully acidified to pH 3-5 with 5N HCl (aq). The resultant slurry was then filtered and the precipitate was rinsed with water and then methanol. The resultant precipitate was dried in a vac-oven overnight, to give 203.6 g (83%, over two steps) of 4-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)-6-chloro-1,5-naphthyridine-3-carboxylic acid (55).

Provenance & Evidence