Diisopropylethylamine → 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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A solution of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine, previously described in WO2007036733A1, (250 mg, 0.83 mmol) in DMF (70 mL) was treated with 3-[(methyloxy)carbonyl]benzoic acid (149 mg, 0.83 mmol), PyBOP (473 mg, 0.91 mmol) and diisopropylethylamine (0.573 mL, 3.3 mmol) and the mixture was stirred at ambient temperature under a nitrogen atmosphere for 4 h. The mixture was then concentrated to dryness and the residue treated with water (150 mL) and extracted with dichloromethane (2×100 mL). The combined organics were dried (hydrophobic frit) and concentrated to dryness to afford 383 mg of the title compound. LC-MS m/z 466 (M+H)+, 0.90 min (ret time).

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