Ethylamine → N-ethyl-4-methyl-3-(1-morpholinophthalazin-6-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

4-Methyl-3-(1-morpholinophthalazin-6-yl)benzoic acid (100 mg, 286 μmol) was dissolved in thionyl chloride (5.7 mL) and heated to 65° C. for 1 h before being concentrated in vacuo. The concentrate was dissolved in THF (5.7 mL), and DIPEA (150 μL, 859 μmol) and ethylamine—2 M in THF (0.71 mL) were added at 0° C. The reaction mixture was warmed to RT and stirred for 3 h, then diluted with 50 mL of ethyl acetate, added to a separation funnel, partitioned with sodium bicarbonate (saturated, aqueous), washed 3× with 50 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated in vacuo to give a crude residue, which was purified by chromatography to afford the title compound. MS (ES+): 377(M+H)+.

Provenance & Evidence