Diisopropylethylamine → HCID 59276173, compound

Participants

Reaction Steps

N,N-Di-tert-butoxycarbonyl-5-((3-oxopiperazinyl)methyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. Methanesulfonic anhydride (0.374 g, 2.147 mmol) was added to a stirred solution of N,N-di-tert-butoxycarbonyl-5-hydroxymethyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.652 g, 1.789 mmol) and N,N-diisopropylethylamine (0.935 mL, 5.37 mmol) in dichloromethane (15 mL). The resulting light yellow solution was stirred at room temperature under nitrogen for 30 min and then piperazin-2-one (0.269 g, 2.68 mmol) was added. The resulting mixture was stirred and heated at 50° C. under a reflux condenser under nitrogen for 5.5 h. The resulting mixture was purified using flash chromatography (Biotage) (0-10% methanol in dichloromethane) to give the desired product (0.764 g, 1.711 mmol, 96% yield) as a white foam-solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 7.71-7.83 (m, 3H), 7.31 (dd, J=1.37, 6.83 Hz, 1H), 4.08 (s, 2H), 3.17-3.23 (m, 2H), 3.14 (s, 2H), 2.74 (t, J=5.47 Hz, 2H), 1.40 (s, 18H); MS (ESI) m/z 447.3 [M+1]+.

Provenance & Evidence