Reaction Steps
To a suspension of N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,6-difluorobenzamide (100 mg, 0.22 mmol) (prepared according to a procedure similar to that described in Example 27, Step C) and 2-methyl-1,2,3,4-tetrahydro-7-isoquinolinamine (44 mg, 0.27 mmol) in 2-propanol (3 mL) was added 2 drops of concentrated HCl. The mixture was stirred at 90° C. overnight, and the reaction mixture was partitioned between saturated aqueous NaHCO3 and 4:1 CHCl3/MeOH. The organic layer was dried over MgSO4, filtered, and purified by flash chromatography to give the title compound as a yellow oil (76 mg, 59% yield). 1H NMR (400 MHz, d6-DMSO): δ 10.95 (s, 1H), 9.44 (s, 1H), 8.85 (d, J=7.0 Hz, 1H), 8.46 (d, J=9.0 Hz, 1H), 8.26 (d, J=5.3 Hz, 1H), 8.02 (s, 1H), 7.83 (d, J=9.2 Hz, 1H), 7.55-7.65 (m, 1H), 7.45-7.49 (m, 2H), 7.35-7.39 (m, 1H), 7.26 (t, J=8.1 Hz, 2H), 7.14 (t, J=6.8 Hz, 1H), 6.97 (d, J=8.4 Hz, 1H), 6.72 (d, J=8.0 Hz, 1H), 6.52 (d, J=5.3 Hz, 1H), 6.35 (d, J=8.0 Hz, 1H), 6.21 (s, 1H), 3.30 (s, 2H) 2.75 (t, J=5.5 Hz, 2H), 2.52-2.63 (m, 2H), 2.26 (s, 3H). MS (ESI) m/z=588 [M+H]+.
