Ethanol, 2-(aminooxy)- → HCID 89451604, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-(3-(morpholinomethyl)quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethanone hydrochloride (79.3) (23 mg, 0.047 mmol) and 2-(aminooxy)ethanol (10.80 mg, 0.140 mmol) in MeOH (5 ml) was added 2 drops of HCl (2 N) by a 1-ml syringe to reach pH about 3 and the mixture was stirred in a sealed tube at 85° C. for 3 h. The mixture was evaporated to dryness and the residue was dissolved in water. The solution was neutralized by adding solid NaHCO3 until pH reached 9, then extracted by DCM (3×). The combined organic layers were washed by water again, dried over Na2SO4, filtered and evaporated. The residue was purified by preparative base HPLC (gradient eluent NB from 20/80 to 95/5. mobile phase A: NH4OH/CH3CN 0.04%; mobile phase B: NH4OH/H2O 0.04%). The desired fractions were collected, evaporated by BUCHI under 30 mbar at 35° C. to remove CH3CN. The remained solution was lyophilized to afford the title compound (12.2 mg, yield 54.2%).

Provenance & Evidence