To a solution of 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-{3-[(dimethylamino)methyl]phenyl}-2-pyrimidinamine (50 mg, 0.115 mmol) (see Example 24, Step A) in 5:1 THF:DMA (2 mL) was added HOBT (46 mg, 0.34 mmol), 0.28 g polystyrene-bound carbodiimide resin (280 mg, 0.34 mmol), and (5-methyl-2-phenyl-1,3-thiazol-4-yl)acetic acid (80 mg, 0.34 mmol). After stirring at rt for 48 h, excess Dowex 550A OH anion-exchange resin was added and the resulting mixture was allowed to stir overnight. The solids were then removed by vacuum filtration and rinsed with THF (25 mL) and MeOH (25 mL). The filtrate was concentrated under reduced pressure and purified by column chromatography (DCM: 0-100% 90:9:1 DCM:MeOH:NH4OH(aq)) to afford the title compound (50.1 mg, 67%). 1H NMR (400 MHz, DMSO-d6) δ 2.11 (s, 6H), 2.43 (s, 3H), 3.31 (s, 2H), 3.81 (s, 2H), 6.45 (d, 1H, J=5.31 Hz), 6.84 (d, 1H, J=6.96 Hz), 7.08-7.11 (m, 1H), 7.14-7.18 (m, 1H), 7.23-7.25 (m, 1H), 7.38-7.46 (m, 5H), 7.59-7.62 (m, 1H), 7.68 (s, 1H), 7.75-7.81 (m, 3H), 7.89 (s, 1H), 8.21 (d, 1H, J=5.49 Hz), 8.48-8.51 (m, 1H), 8.79 (d, 1H, J=6.96 Hz) 9.50 (s, 1H), 10.35 (s, 1H). ES-LC/MS m/z=651 [M+H]+.
