Methyl iodide → N-benzyl-N-methyl-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-1-amine

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Reaction Steps

To a solution of tert-butyl 4-{4-[1-(benzylamino)-1H-pyrrolo[3,2-b]pyridin-6-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate (prepared in example 25: 125 mg, 0.26 mmol) in 3.0 mL of DMF at 0° C. was added NaH (60% in oil, 31 mg, 0.78 mmol) in one portion. After 15 min, the mixture was treated with methyl iodide. HPLC check shows disappearance of starting material. Solvent was removed and the residue dissolved in ethyl acetate, washed with aqueous NaHCO3. The organic solution was dried, evaporated and then the residue was treated with methanol (0.5 mL) and HCl (4.0M in dioxane, 2.0 mL) at room temperature for 30 min. The solvent was removed and the residue was purified by preparative HPLC to give product as a white solid (4.1 mg, yield 4%).

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