Triethylamine → N-[6-amino-pyridin-3-yl]-hexanamide

Participants

Reaction Steps

Hexanoyl chloride (1.1 equiv., 10.08 mmol, 1.36 g) was added dropwise to a cooled (0° C.) suspension of 2,5-diaminopyridine (I13) (1.0 equiv., 9.16 mmol, 1.00 g) and triethylamine (1.1 equiv., 10.08 mmol, 1.02 g) in chloroform (100 ml). The reaction mixture was stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure, and the residue was brought on a filter and successively washed with saturated NaHCO3 solution, water and isopropyl ether. The crude product was further purified by column chromatography (dichloromethane/methanol 95:5; Rf=0.3) to give N-[6-amino-pyridin-3-yl]-hexanamide (I14) (1.24 g, yield=65%). 1H NMR (6, DMSO-D6): 0.87 (3H, t, J=6.9), 1.23-1.33 (4H, m), 1.53-1.60 (2H, m), 2.22 (2H, t, J=7.5 Hz), 5.67 (2H, s), 6.39 (1H, d, J=8.8 Hz), 7.54 (1H, dd, J=8.8, 2.6 Hz), 8.05 (1H, d, J=2.5 Hz), 9.53 (1H, s)

Provenance & Evidence