Combined 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (50 mg, 0.163 mmol), EDC (46.9 mg, 0.245 mmol) and HOBT (37.5 mg, 0.245 mmol) and DMA (1 mL), and treated with Hunig's base (0.114 ml, 0.653 mmol) and stirred at ambient temperature for 5 minutes, then added to 4-amino-1-Boc-piperidine (38.5 mg, 0.327 mmol) and stirred at room temperature overnight. The reaction mixture was then diluted to a total volume of about 1.5 mL with methanol and purified via prep HPLC. The product containing fractions were collected and concentrated in vacuum to give a residue which was treated with TFA (2 mL) in DCM (2 mL). After stirring at ambient temperature overnight the reaction was concentrated in vacuo and dried under vacuum to give the title compound (39.3 mg, 62%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.65-1.82 (m, 2 H) 1.93-2.08 (m, 2H) 2.94-3.16 (m, 2 H) 3.35 (d, J=12.63 Hz, 2 H) 3.99-4.19 (m, 1 H) 7.80 (d, J=8.59 Hz, 2H) 8.15 (d, J=7.33 Hz, 2 H) 8.29-8.78 (m, 6 H) 8.87-8.99 (m, 1 H) 13.59 (br. s., 1 H). MS m/z [M+H]+ 389.2.
