Water → tert-butyl(1-(4-(3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-5,6-dihydro-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl)cyclobutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(5-hydrazono-3-phenyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)phenyl)cyclobutyl)carbamate (22 mg, 0.04 mmol) in dry DMF (1 mL) was added EDCI (11 mg, 0.06 mmol), HOBt.H2O (8 mg, 0.06 mmol) and 1-methyl-1H-imidazole-4-carboxylic acid (8 mg, 0.06 mmol) under nitrogen. The reaction mixture was heated at 60° C. overnight. After cooled down to room temperature, the mixture was partitioned between saturated NaHCO3 solution and ethyl acetate. The layers were separated and the organic phase washed with water and brine, dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (method G, gradient 5 to 95% 0.1% FA/ACN in 0.1% FA/H2O) to give the title compound (1 mg, 5%). 1H NMR (500 MHz, CDCl3): 8.49 (1H, s), 7.74 (1H, s), 7.54 (1H, s), 7.38 (2H, d), 7.31 (2H, d), 7.28-7.23 (5H, m), 5.01 (1H, br s), 4.94 (2H, t), 3.81 (3H, s), 3.49 (2H, t), 2.60-2.30 (4H, m), 2.10-2.01 (1H, m), 1.85-1.76 (1H, m), 1.45-1.20 (9H, br).

Provenance & Evidence