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 via rotovap. The crude reaction was dissolved in tetrahydrofuran 99.9% (5.7 mL) and diisopropylethylamine (150 μL, 859 μmol) and ethylamine—2 M in THF (0.71 mL) was added at 0° C. The reaction mixture was warmed to ambient temperature and stirred for 3 h. The reaction mixture was diluted with 50 mL of EtOAc, added to an addition funnel, partitioned with sodium bicarbonate (saturated, aqueous). The organic layers were washed 3 times with 50 mL of sodium bicarbonate (saturated, aqueous), combined, dried over sodium sulfate, and concentrated via rotovap to give a crude product. After purification by chromatography, the title compound was obtained. Found MS (ES+): 377(M+H)+.

Provenance & Evidence