1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-(6-Aminopyridin-3-yl)(3-methylmorpholino)methanone

Participants

Reaction Steps

To a solution of (R)-3-methylmorpholine (2.02 g, 20 mmol) in ethanol (25 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) (3.33 g, 17.4 mmol), hydroxybenzotriazole (HOBt) (2.35 g, 17.4 mmol), and 6-aminonicotinic acid (2.0 g, 14.5 mmol). After stirring for 18 h at room temperature, the reaction suspension was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 3:1 ethyl acetate/petroleum ether to afford 132a as a white solid (1.6 g, 36%). MS-ESI: [M+H]+ 222.3.

Provenance & Evidence