Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 66599202, compound

Participants

Reaction Steps

4-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-2-piperazinone (I37) (90 mg, 0.309 mmol) was suspended in dichloromethane (DCM) (1.5 mL) before treating with trimethyloxonium tetrafluoroborate (57.8 mg, 0.371 mmol) and stirring for 16 hours at RT under argon before adding 4-methyl-3-isothiazolecarbohydrazide (I129)(58.3 mg, 0.371 mmol) and stirring for 4 hours. Adding 1-butanol (1.500 mL) then removing the DCM by evaporation before heating at 110° C. for 3 hours. As LCMS indicated that some start material remained, the reaction mixture was left heating for a further 17 hours. The reaction was worked up by diluting with DCM (30 ml) and washing with saturated sodium bicarbonate solution (30 ml). The aqueous layer was extracted with DCM (2×20 ml), the combined extracts were washed with brine (20 ml), dried (MgSO4), filtered and evaporated to afford a brown gum, 120 mg. The gum was purified by MDAP, the desired fraction isolated and the solvent evaporated to afford a white solid. The solid dried over the weekend in the vac oven at 40° C. to afford an off white solid of desired product in 22 mg.

Provenance & Evidence