3-Fluorophenol → HCID 11442642, compound

Participants

Reaction Conditions

Reaction Steps

A solution containing 3-fluorophenol (1.5 eq.) in DMF was treated with sodium hydride (60% oil dispersion, 4 eq.) for 2 hours at around 50° C. A solution containing containing methanesulfonic acid 2-(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)-octahydro-pyrido[1,2-a]pyrazin-7-ylmethyl ester (1 eq., see subpart (a) above) in DMF was added. The resulting mixture was then heated at around 100° C. for 24 hours. The solvent was removed, and the residue was dissolved in DMSO, filtered and purified by preparative HPLC using aqueous CH3CN (buffered with 0.1% TFA) to afford the desired product as a white powder: 1H NMR (400 Hz, DMSO-d6) δ 7.96 (d, J=2.0 Hz, 1H), 7.39 (m, 1H), 7.15 (d, J=3.0 Hz, 1H), 6.92-6.83 (m, 3H), 6.75 (dd, J=3.0, 2.0 Hz, 1H), 4.84 (m, 2H), 4.08 (dd, J=10.0, 5.0 Hz, 1H), 3.74 (dd, J=10.0, 7.0 Hz, 1H), 3.65 (m, 2H), 3.33 (m, 3H), 3.10 (m, 1H), 2.97 (m, 1H), 2.39 (m, 1H), 1.99 (m, 2H), 1.67 (m, 1H), 1.48 (m, 1H). MS m/z: 465 [M+H]+.

Provenance & Evidence