Acetic Acid → HCID 178509611, compound

Participants

Reaction Conditions

Reaction Steps

Combined N-benzyl-6-hydrazinylnicotinamide (53.3 mg, 0.220 mmol) and ethyl 2-(4-cyano-2-fluorophenyl)-3-(dimethylamino)acrylate (75 mg, 0.286 mmol) in 2-propanol (1 mL) and added acetic acid (0.038 mL, 0.660 mmol) at 23° C. The reaction mixture was stirred at 23° C. for 18.5 hours, Hunig's base (0.230 mL, 1.320 mmol) was added, and the reaction mixture was stirred at 60° C. for 6 hours. The reaction mixture was cooled to 23° C. and concentrated via rotary evaporation to furnish a brown oil which was dissolved in DMSO (1 mL), filtered through a Hydrophilic PTFE 0.45 μm filter (Millipore Millex™-LCR), rinsed with DMSO (2×0.5 mL), and purified via preparative HPLC (SunFire™ C18, 5 μm, ID 30 mm×75 mm) using a gradient of 50-80% ACN (with 0.035% TFA) in water (with 0.05% TFA). Product containing fractions were combined and concentrated via rotary evaporation to furnish an off-white solid which was collected by filtration, rinsed with water (5×2 mL), and dried in vacuo to give the title compound (9.1 mg, 10.01% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.53 (d, J=5.81 Hz, 2H) 7.21-7.40 (m, 5H) 7.72 (dd, J=8.34, 1.52 Hz, 1H) 7.87 (dd, J=11.75, 1.39 Hz, 1H) 8.29 (br. s., 1H) 8.42-8.54 (m, 2H) 8.60 (br. s., 1H) 8.95-9.03 (m, 1H) 9.29 (t, J=5.94 Hz, 1H) 13.78 (br. s., 1H). MS m/z [M+H]+ 414.3.

Provenance & Evidence