CNC(=O)c1ccccc1Nc1cc(Cl)ncc1C#N.Cc1nn(C)cc1N>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1C#N2-(2-chloro-5-cyanopyridin-4-ylamino)-N-methylbenzamide (200 mg, 0.70 mmol), Palladium(II) acetate (12.53 mg, 0.06 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (155 mg, 1.40 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (48.4 mg, 0.08 mmol) and Cesium carbonate (273 mg, 0.84 mmol) were suspended in dioxane (5 mL) into a test tube. The reaction was purged for 5 mins with nitrogen and then heated to 90 °C for 24 hours with stirring. The reaction was cooled to cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired crude product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford crude product .The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 2-(5-cyano-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-N-methylbenzamide (126 mg, 50.0 %) as a beige solid.
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