Hydrochloric Acid → 2-[4-(1-Azido-1-methylethyl)phenyl]-5-methoxy-3-(2-thienyl)-1,6-naphthyridine

Participants

Reaction Conditions

Reaction Steps

Sodium methoxide (25 weight % in methanol, 0.23 mL) was added to a stirred mixture of 1-[4-(1-azido-1-methylethyl)phenyl]-2-(2-thienyl)ethanone (2-4, 95mg, 0.33mmol) and tert-butyl(2-chloro-3-formylpyridin-4-yl)carbamate (1-3, 100 mg, 0.39 mmol) in methanol (2 mL), then heated to 65° C. for 2 h. The mixture was cooled to rt, diluted with EtOAc, and acidified with 1N HCl. The aqueous was extracted with ethyl acetate and the combined organics were washed with 1:1 brine:water, dried over magnesium sulfate, filtered, and concentrated to give a dark semi-solid. The crude product was purified via automated silica gel chromatography (0-45% EtOAc in hexane with 5% CH2Cl2 over 30 min) to give the title compound as an amber oil. LRMS m/z (M+1) Calcd: 402.2,. Found 402.2.

Provenance & Evidence