Tetrahydrofuran → HCID 58137757, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-(2-(4-(tert-butoxycarbonylamino)benzoyl)hydrazinyl)-6-chloropyridazine-4-carboxylate (66C) (1.49 g, 3.20 mmol) in a mixed solvent of THF (10 mL) and CCl4 (5 mL) at 0° C. under argon was added Et3P (3.35 mL, 19.2 mmol), followed by DIPEA (3.35 mL, 19.2 mmol). The reaction mixture was stirred at 0° C. for 10 min. Analysis by LC/MS indicated the starting material was consumed. The reaction mixture was partitioned between EtOAc and water, the separated EtOAc layer washed with water, saturated aqueous NaHCO3, saturated aqueous NaCl (2×), dried (anhydrous Na2SO4), and concentrated. The crude residue was purified using a silica gel cartridge (40 g) which was pretreated with 1% Et3N in hexanes for 10 min at 10 mL/min, eluting with a gradient of EtOAc (0-50%) in hexanes to afford 1.02 g (71%) of the title compound as a yellow solid. HPLC/MS (Method B): retention time=3.78 min, [M+H]+=446.3.

Provenance & Evidence