In a 25 mL sealable tube under nitrogen were combined 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid (370 mg, 1.2 mmol) and 3-(aminomethyl)-4-ethyl-6-methyl-2(1H)-pyridinone.HCl (340 mg, 1.68 mmol) in DMSO (3 mL). 1-hydroxy-7-azabenzotriazole (277 mg, 2.04 mmol) was added and the resulting mixture was degassed with nitrogen for 10 minutes. N-methylmorpholine (0.55 ml, 5 mmol) and EDC (390 mg, 2 mmol) were added, the vessel was sealed, and the mixture was stirred at room temperature overnight. The mixture was poured onto 10 mL of ice-water and solids crashed out. 10% K2CO3 was added to adjust the pH˜8-9. The mixture was stirred for 4 hours and then allowed to stand for another 2 hours. Solids were filtered and air-dried. DMF along with some water was then added. Solids that precipitated were filtered and dried to afford the title compound as a light orange solid (515 mg, 91%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 1H) 8.63 (t, J=4.80 Hz, 1H) 8.36 (s, 1H) 8.20 (s, 1H) 7.70 (d, J=1.52 Hz, 1H) 5.93 (s, 1H) 5.23 (t, J=7.07 Hz, 1H) 4.36 (s, 1H) 4.35 (s, 1H) 2.53-2.59 (m, 2H) 2.14 (s, 3H) 2.07-2.13 (m, 2H) 1.93-2.01 (m, 2H) 1.83-1.91 (m, 2H) 1.65-1.73 (m, 2H) 1.10 (t, J=7.58 Hz, 3H); LC-MS (ES) m/z=456.9/459.1
