Acetic Acid → HCID 72706323, compound

Participants

Reaction Steps

9-Acetyl-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 81, 67 mg, 0.19 mmol), (2S,6R)-2,6-dimethylmorpholine (0.060 mL, 0.49 mmol), ACN (1 mL) and acetic acid (0.020 mL, 0.35 mmol) were combined and stirred for 10 minutes. Sodium cyanoborohydride (18 mg, 0.29 mmol) was added and the mixture was stirred for 3 days at 50° C. The mixture was filtered. Purification (HPLC, 10-65% ACN in water) afforded the title compound (26 mg, 23%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.19 (d, J=6.27 Hz, 3H), 1.23 (d, J=6.27 Hz, 3H), 1.92 (d, J=7.03 Hz, 3H), 2.34 (td, J=11.01, 2.32 Hz, 2H), 3.32 (d, J=11.42 Hz, 1H), 3.57 (d, J=11.42 Hz, 1H), 3.77 (s, 3H), 4.12 (d, J=7.03 Hz, 2H), 4.54 (q, J=6.86 Hz, 1H), 5.75 (s, 2H), 6.85 (d, J=8.66 Hz, 2H), 7.62 (d, J=8.66 Hz, 2H), 8.40 (s, 1H), 8.74 (s, 1H), 8.95 (s, 1H). [M+H]=449.3.

Provenance & Evidence