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

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Reaction Steps

To 3-(methoxycarbonyl)benzoic acid (1.261 g, 7.00 mmol) in DCM (35 mL) was added TEA (2.439 mL, 17.50 mmol), EtOCOCl (0.739 mL, 7.70 mmol) at 0° C. after which 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (2.379 g, 7.00 mmol) was added. This mixture was then stirred for 1 h at room temperature. The reaction mixture was diluted with DCM (35 mL) then washed with HOAc (2×20 mL, 10%), NaHCO3 (20 mL, 10%), and water (20 mL), concentrated, The residue washed with EtOAc/Hexane (10 mL, 1:1) to afford the title compound (3.5138 g, 94.2%). LC-MS m/z 466 (M+H)+.

Provenance & Evidence