Diisopropylethylamine → Methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoate

Participants

Reaction Steps

To a solution of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (0.6 g, 2 mmol) stirring at room temperature under argon in DMF (150 mL) was added 3-[(methyloxy)carbonyl]benzoic acid (0.356 g, 2 mmol), followed by PyBOP (1.14 g, 2.2 mmol), and N,N-diisopropylethylamine (1.38 mL, 8 mmol). The mixture was stirred at room temperature for 17 h. The solvent was pumped off, and the residue taken up in CH2Cl2 (300 mL), and washed with water (300 mL). The organic phase dried over anhydrous Na2SO4, filtered and concentrated. This was then CombiFlashed on a 40 gram silica column eluted with 20-100% EtOAc to afford the title compound. LC-MS m/z 465.8 (M+H)+, 1.49 min (ret time).

Provenance & Evidence