Diisopropylethylamine → 2-Pyridineacetic acid, hydrochloride (1:1)

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2-Pyridylacetic acid hydrochloride (0.033 g, 0.191 mmol), HATU (0.084 g, 0.220 mmol) and DIPEA (0.130 ml, 0.764 mmol) were combined in DMF (3 ml) and stirred at 20° C. for 10 minutes. 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (0.07 g, 0.20 mmol) was added and the reaction was stirred for 5 h at 20° C. A second batch of 2-pyridylacetic acid hydrochloride (0.033 g, 0.191 mmol), HATU (0.084 g, 0.220 mmol) and DI PEA (0.130 ml, 0.764 mmol) in DMF (3 ml) was prepared and stirred at 20° C. for 10 minutes. It was added to the main reaction mixture and stirred for 3 days (weekend) at 20° C. The reaction mixture was applied to a 5 g NH2-SPE cartridge and eluted with 10% methanol in dichloromethane. The solvent was evaporated and the residue was purified by Mass Directed Auto Prep (Method B) to give the title compound (0.018 g).

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