Hydrochloric Acid → HCID 118036250, compound

Participants

Reaction Steps

A solution of 7-(dimethoxymethyl)-N-(5-(trifluoromethyl)pyridin-2-yl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 1, 64.5 mg, 0.163 mmol) in THF (0.4 ml) at room temperature was treated with water (0.6 ml) and conc. HCl (0.20 ml). After the addition, additional THF (0.2 ml) was added and the reaction mixture was stirred at room temperature for 2.5 h. Subsequently, NMP (0.1 ml) was added followed by TFA (0.10 ml, 1.3 mmol) and the resulting solution was stirred for 2 h. The reaction was then quenched by the addition of sat. aq. NaHCO3 (gas evolution) and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a white solid.

Provenance & Evidence