Ethanol, 2-(aminooxy)-, hydrochloride → 2-[(E)-1-[3-[1-(5,7-difluoroquinolin-6-yl)ethyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]oxyethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(1-(1-(5,7-difluoroquinolin-6-yl)ethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (76.5 mg, 0.22 mmol) in MeOH (50 mL) was added 2-(aminooxy)ethanol hydrochloride (49.0 mg, 0.43 mol). The mixture was heated at 45° C. overnight. The solvent was removed under reduced pressure. The residue was purified by column chromatography with gradient (DCM/MeOH=10:1) to give the title compound as a white solid (58.0 mg, 62%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.23 (s, 1H), 9.01 (dd, 1H), 8.52 (d, 1H), 7.74 (d, 1H), 7.63 (dd, 1H), 6.80 (q, 1H), 4.74 (t, 1H), 4.27 (t, 2H), 3.68 (m, 2H), 2.36 (d, 3H), 2.10 (s, 3H). LCMS (method A): [MH]+=414, tR=5.44 min.

Provenance & Evidence