Ammonium Chloride → HCID 22025333, compound

Participants

Reaction Conditions

Reaction Steps

2-(Diphenylmethylenamino)-N-(4-phenyl-butyl)-acetamide (7) (0.57 g, 1.5 mmol) is dissolved in dry THF (5 mL) and cooled to −78° C. A solution of KHMDS (0.5 M in PhMe, 3.0 mL, 1.5 mmol) is added slowly to the imide. The solution is warmed to 0° C. and then cooled to −78° C. A solution of 1-benzenesulfonyl-4-bromomethyl-6-chloro-7-methoxy-1H-indazole (0.57 g, 1.4 mmol) in dry THF (4 mL) is added slowly at −78° C. and the solution is allowed to stir 15 min. The reactio is then poured into a solution of aqueous NH4Cl and extracted with EtOAc. The organic phase is washed with water, brine, dried over MgSO4 and concentrated. The crude reaction is purified by column chromatography (silica, 10–20% EtOAc/PhMe) to provide 3-(1-benzenesulfonyl-6-chloro-7-methoxy-1H-indazol-4-yl)-2-(diphenylmethylenamino)-N-(4-phenyl-butyl)-propionamide.

Provenance & Evidence