Diisopropylamine → HCID 58071878, compound

Participants

Reaction Conditions

Reaction Steps

200 mg Trifluoro-methanesulfonic acid 7-[3-methoxy-4-(tetrahydro-pyran-4-yloxy)-phenyl]-[1,6]naphthyridine-5-yl ester (6.6) was placed in 3 mL dimethylacetamide at ambient temperature before 51 mg 5-amino-1H-pyridine-2-one (2.31) and 109 mg N,N-diisopropylamine was added. The reaction was heated to 70° C. overnight in a sealed tube and then cooled to ambient temperature. After this time, additional 5-amino-1H-pyridin-2-one was added and the reaction was heated to 100° C. for 6 h, cooled to ambient temperature overnight. The reaction was then heated again at 100° C. for 24 h and then additional N,N-diisopropylamine was added and heating continued for 24 h. The reaction mixture was then cooled to ambient temperature and partitioned between water and ethyl acetate. The organic phase was separated and the aqueous phase was extracted with additional ethyl acetate (×3) and the combined organic fractions were dried, filtered and the solvent was concentrated from the filtrate under reduced pressure. Purification by silica gel chromatography (ethyl acetate/methanol: 95:5) and then by preparative HPLC provided the title compound.

Provenance & Evidence