Hydrochloric Acid → HCID 10792343, compound

Participants

Reaction Steps

To a solution of 5-methoxycarbonyl-N1-(3-cyanobenzoyl)]-N2-(4-t-butylbenzoyl)-1,2-benzenediamine (2.6 g, 5.7 mmol) in THF (80 mL) was added methanol (27 mL), followed by a solution of LiOH.H2O (1 g, 22.8 mmol) in water (27 mL). After 12 h, the pH was adjusted to 3 with conc HCl and the mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with 1 N HCl, brine (2×), MgSO4 dried, and concentrated. To the residue dissolved in DMF (20 mL) was added benzyl bromide (1.06 g, 6.2 mmol), followed by K2CO3 (1.6 g, 11.4 mmol). After 3 h, the reaction was concentrated and the residue was dissolved in ethyl acetate and washed with satd aq NaHCO3 followed by brine. The organic layer was MgSO4 dried and 5 g of silica gel was added. This mixture was concentrated and chromatographed (20% ethyl acetate/hexanes to 60% ethyl acetate/hexanes) to give the title compound as a white solid (1.2 g, 40%); MS(FD): 531.0.

Provenance & Evidence