Reaction Steps
A mixture of 2-chloro-1-{4-[5-(1-methyl-1H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-3,6-dihydro-2H-pyridin-1-yl}-ethanone (8BW) (0.522 gm, 0.863 mmol), 3-Methylsulfanyl-pyrrolidine-3-carboxylic acid [3-(6-isopropoxy-pyridin-3-yl)-1H-indazol-5-yl]-amide (8BO) (0.463 gm, 0.95 mmol), and DIEA (0.9 ml, 5.2 mmol) in DMF (10 ml) was stirred at room temperature for overnight. DMF was removed under reduced pressure. The crude reaction mixture was precipitated in 30 ml ice cold water, filtered, dried, and purified by column chromatography using 10% MeOH/EtOAc to get desired product A24 as a yellow solid (70%). (LCMS M+1=698, ret. time=3.6 min.) 1H NMR (400 MHz, DMSO):8.67 (S, 1H), 8.64 (S, 1H), 8.36 (S, 1H), 8.15 (S, 1H), 7.64 (d, 1H, J=8.8 Hz), 7.52 (S, 1H), 7.49 (d, 1H J=5.2 Hz), 7.40 (d, 1H J=8.8 Hz), 7.02 (m, 1H), 6.18 (d, 1H, J=18.8 Hz), 5.08 (m, 1H), 4.41 (d, 2H, J=7.6 Hz), 4.34 (d, 1H, J=6.4 Hz)), 4.12 (S, 1H), 3.96 (s, 2H), 3.84 (S, 3H), 3.76 (S, 2H), 3.52 (S, 2H), 2.76 (S, 1H), 2.58 (d, 2H J=20.4 Hz), 2.13 (S, 3H), 1.94 (t, 2H J=2.8 Hz), 1.39 (d, 6H, J=4.8 Hz).
