Water → Ammonia

Participants

Reaction Conditions

Reaction Steps

100 mg Trifluoro-methanesulfonic acid 7-(3,4,5-trimethoxy-phenyl)-[1,6]naphthyridine-5-yl ester (6.1) was placed in 3 mL dimethylacetamide at ambient temperature before 111 mg 5-amino-1H-pyridine-2-one (2.31) was added. The reaction was heated to 70° C. overnight and then cooled to ambient temperature. 1.3 mL N,N-Diisopropylamine was added and the reaction was heated to 100° C. overnight. After this time, the reaction was heated to 120° C. and stirred overnight. The mixture was then cooled to ambient temperature and water was added. The mixture was extracted into ethyl acetate (×3) and the combined organic fractions were washed with water, separated and the solvent was removed under reduced pressure. Purification by preparative HPLC and then by silica gel chromatography (ethyl acetate containing 1-10% of 7M ammonia in methanol) gave the title compound.

Provenance & Evidence