Thiazole-5-carbohydrazide → HCID 66599375, compound

Participants

Reaction Steps

4-[(2,4-Dichloro-3-fluorophenyl)carbonyl]-2-piperazinone (I37) (263 mg, 0.903 mmol) was suspended in dichloromethane (DCM) (2 mL) before treating with triethyloxonium tetrafluoroborate (189 mg, 0.994 mmol) and stirring for 45 mins at RT under argon before adding 1,3-thiazole-5-carbohydrazide (I109)(155 mg, 1.084 mmol) and stirring for 18 hours (overnight). The DCM was removed and the residue was suspended in 1-butanol (2.0 mL) and heated at 110° C. for 3 hours. The reaction was cooled to RT, diluted with DCM (30 ml) and washed with saturated sodium bicarbonate solution (20 ml). The aqueous layers were extracted with DCM (2×20 ml), combined, washed with brine (20 ml), dried (MgSO4), filtered and evaporated to afford a yellow gum of crude product which was purified by MDAP. Desired fractions were isolated and solvent evaporated to afford a colourless gum which solidified when triturated with Et2O to afford a pale yellow solid of desired product in 100 mg.

Provenance & Evidence