Hydrochloric Acid → N-[5-{3-[2-({3-[(dimethylamino)methyl]phenyl}amino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}-2-(methyloxy)phenyl]-2,6-difluorobenzamide

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To a solution of N-[5-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]-2-(methyloxy)phenyl]-2,6-difluorobenzamide (30 mg, 0.06 mmol) in 1,4-dioxane (6 mL) and 2-propanol (3 mL) was added 3-[(dimethylamino)methyl]aniline (27 mg, 0.18 mmol) followed by 4M HCl in dioxane (0.076 ml, 0.31 mmol). After heating overnight at 80° C., the reaction was quenched with saturated NaHCO3 (25 mL), solvent removed by rotary evaporation, the aqueous layer extracted with DCM (25 mL), organic layer concentrated, and purified by column chromatography (5-50% EtOAc in hexanes) to provide the product (12.8 mg, 35%) as an off-white solid. ESIMS (M+H)+=606. 1H NMR (400 MHz, DMSO-d6) δ 2.12 (s, 6H), 3.33 (bs, 2H), 3.86 (s, 3H), 6.57 (d, 1H, J=5.49 Hz), 6.85 (d, 1H, J=7.14 Hz), 7.07-7.10 (t, J=6.78 Hz, 1H), 7.15-7.19 (m, 4H), 7.35-7.38 (m, 1H), 7.41-7.45 (m, 1H), 7.50-7.54 (m, 1H), 7.63 (d, 1H, J=6.78 Hz), 7.69 (s, 1H), 8.23 (d, 1H, J=5.49 Hz), 8.32 (s, 1H), 8.49-8.50 (m, 1H), 8.80-8.82 (m, 1H), 9.50 (s, 1H), 10.19 (s, 1H).

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