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

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (3.5 mg, 0.01 mmol) in MeOH (1 mL), 2-(aminooxy)ethanol hydrochloride (intermediate S) (1.6 mg, 0.02 mmol) was added, the solution was heated to 50° C. for overnight. The solvent was removed in vacuo. The residue was diluted with water, treated with aqueous NaHCO3 solution, extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by prepared HPLC to give white solid (E)-1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone O-2-hydroxyethyl oxime (2.4 mg, 56%). 1H-NMR (400 MHz, CDCl3) δ ppm 9.38 (s, 1H), 8.98 (d, 1H), 8.42 (d, 1H), 7.64 (d, 1H), 7.48 (m, 1H), 6.18 (s, 2H), 4.45 (m, 2H), 3.98 (m, 2H), 2.36 (s, 3H), 1.96 (m, 1H). LCMS (method B): [MH]+=399.9, tR=2.19 min.

Provenance & Evidence