Benzenamine, 4-(4-morpholinyl)- → HCID 22124684, compound

Participants

Reaction Steps

A stirred solution of (XV, where R2 is ethyl) (100 mg, 0.52 mmol), 4-(4-morpholinyl)aniline (0.26 g, 1.1 mmol) in THF (5.0 mL) under nitrogen at -78° C. was treated with a solution (0.8 mL, 1.2 mmol) of lithium diisopropylamide (1.5 M in cyclohexane), then the temperature was allowed to rise slowly to 20° C. overnight. The resulting solution was treated with 3 drops of glacial acetic acid and concentrated to a dark residue that was purified that purified by silica gel chromatography eluting with EtOAc. The product fractions were pooled and concentrated to a solid that was crystallized to give 1-ethyl-7-(4-(morpholin-4-yl)phenylamino)-1H-[1,6]naphthyridin-2-one (94 mg, 52%): mp (2-propanol/hexanes) 219-223° C.

Provenance & Evidence