Combined 6-hydrazinyl-N-((tetrahydro-2H-pyran-4-yl)methyl)nicotinamide (107 mg, 0.427 mmol) and ethyl 2-(4-cyano-1H-pyrazol-1-yl)-3-(dimethylamino)acrylate (100 mg, 0.427 mmol) in 2-propanol (1423 μl) and treated with 1.85N HCl (841 mg, 0.427 mmol). The resulting clear mixture was stirred overnight (15 h) and then Hunig's base (297 μl, 1.708 mmol) was added and the reaction was stirred at ambient temperature for 2.5 h. The reaction mixture was then concentrated in vacuo and purified using HPLC (20-95% ACN in water, TFA-buffered). Product-containing fractions were concentrated in vacuo to give a solid (volume ˜20 mL). The solid was filtered and dried in vacuum to give the title compound (57.4 mg, 34.2% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22 (qd, J=12.21, 4.29 Hz, 2 H) 1.62 (d, J=12.88 Hz, 2 H) 1.81 (m, J=10.96, 7.29, 3.76, 3.76 Hz, 1 H) 3.20 (t, 2 H) 3.27 (t, J=10.86 Hz, 2 H) 3.86 (dd, J=11.24, 2.65 Hz, 2 H) 8.29 (s, 1 H) 8.42 (br. s., 3 H) 8.74 (t, J=5.68 Hz, 1 H) 8.93 (s, 2 H) 13.41 (br. s., 1 H). MS m/z [M+H]+ 394.
