4-Toluenesulfonyl chloride → HCID 86729592, compound

Participants

Reaction Steps

A stirred solution of 3-amino-W-(2-(benzyloxy)-3,3,3-trifluoro-2-methylpropanoyl)-5,6-bis(trifluoromethyl)pyrazine-2-carbohydrazide (step 1) (510 mg, 0.982 mmol) in DCM (20 ml) was treated with triethylamine (0.411 ml, 2.95 mmol) and stirred at RT. Tosyl chloride (562 mg, 2.95 mmol) was added and stirring continued for 30 minutes. The reaction mixture was partitioned between EtOAc (50 ml) and 1M HCl (50 ml), shaken and separated. The organic portion was washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo to give a yellow oil. The crude product was purified by mass directed LC-MS eluting with MeCN/Water/0.1% TFA. The clean fractions were poured into EtOAc (50 ml) and washed with saturated NaHCO3 (50 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound as a white crystalline solid.

Provenance & Evidence