Triethylamine → 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

A mixture of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (1.0 g, 2.94 mmol), 3-[(methyloxy)-carbonyl]benzoic acid (0.58 g, 3.24 mmol), HBTU (1.34 g, 3.53 mmol) and Et3N (0.82 mL, 5.89 mmol) in DCM (30 mL) was stirred at room temperature overnight. The reaction was quenched with saturated NaHCO3 and the solution extracted with DCM twice. The combined organic layers were washed with water followed by a brine wash. The organic layer was dried over sodium sulfate, filtered, concentrated and purified using CombiFlash chromatography, eluting with 80% ethyl acetate in hexane. The product fractions were combined and concentrated to give methyl 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-carbonyl]benzoate as an oil (1.40 g, 99%). LC-MS m/z 467 (M+H)+.

Provenance & Evidence