Diisopropylethylamine → HCID 59276353, compound

Participants

Reaction Steps

4-((2-Bromo-[1,2,4]triazolo[1,5-a]pyridin-5-yl)methyl)piperazin-2-one. Methanesulfonic anhydride (0.083 g, 0.479 mmol) was added to a stirred solution of (2-bromo-[1,2,4]triazolo[1,5-a]pyridin-5-yl)methanol (0.095 g, 0.417 mmol) and N,N-diisopropylethylamine (0.218 mL, 1.250 mmol) in N,N-dimethylformamide (2.5 mL). The resulting clear yellow solution was capped and stirred at room temperature. After 40 min more methanesulfonic anhydride (18 mg, 0.103 mmol) was added. The resulting clear yellow solution was capped and stirred at room temperature for an additional 30 min. piperazin-2-one (0.092 g, 0.916 mmol) was added and the resulting clear yellow solution was sealed and stirred at 50° C. for 3.5 h. The resulting mixture was purified using flash chromatography (Biotage) (0-15% methanol in dichloromethane) to give the desired product (0.121 g, 0.390 mmol, 94% yield) as a white solid with some yellow impurity. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 7.84 (br s, 1H), 7.72-7.80 (m, 2H), 7.26-7.34 (m, 1H), 4.08 (s, 2H), 3.18-3.26 (m, 2H), 3.16 (s, 2H), 2.69-2.79 (m, 2H); MS (ESI) m/z 310.0 [M]+, 311.8 [M+2]+.

Provenance & Evidence