5-Hexenoyl chloride → Hex-5-enoic acid (6-methoxy-[1,5]naphthyridin-4-yl)-amide

Participants

Reaction Steps

To a suspension of 6-methoxy-[1,5]naphthyridin-4-ylamine (1.5 g, 8.56 mmol) and TEA (1.55 mL, 1.3 eq.) in DCM (8.5 mL) was added 5-hexenoyl chloride (1.36 g, 1.2 eq.) in DCM (1.5 mL) at rt. The resulting suspension was vigorously stirred at rt for 20 h. The mixture was then washed with water. The org. layer was dried over Na2SO4 and concentrated. The residue was chromatographed on SiO2 (DCM-MeOH—NH4OH: 1000:50:4) to afford the title intermediate as a yellow solid (1.66 g, 71% yield).

Provenance & Evidence