1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(4-fluorophenyl)-N-(6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-yl)-3-oxo-2,3-dihydropyridazine-4-carboxamide

Participants

Reaction Steps

A 25 mL round-bottomed flask was charged with 6-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)pyridin-3-amine (15 mg, 0.0415 mmol), 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (24.3 mg, 0.104 mmol; prepared as in Example 19, Step C) HOBT-H2O (6.36 mg, 0.0415 mmol), EDCI (7.96 mg, 0.0415 mmol), N-ethyl-N-isopropylpropan-2-amine (5.36 mg, 0.0415 mmol) and DMF (3 mL). The reaction mixture was stirred at room temperature for 18 hours. Diluted with water (20 mL) and extracted with EtOAc (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated to obtain product (30 mg, 90%) as a light brown solid. LRMS (esi+) 578 (M+H).

Provenance & Evidence