1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68513136, compound

Participants

Reaction Steps

To a stirred suspension of 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (prepared in Example 19, step C) (7 mg, 0.03 mmol) in 300 μL dichloromethane at room temperature under nitrogen was added DIEA (10 μL, 0.06 mmol) followed by EDCI (5.7 mg, 0.03 mmol) and HOBT-H2O (4.6 mg, 0.03 mmol). After stirring for 10 minutes, a solution of (S)-1-(1-(4-methoxybenzyl)-4-(4-amino-2-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)-N,N-dimethylpyrrolidin-3-amine (9.5 mg, 0.02 mmol) in 300 μL dichloromethane was added. After stirring overnight, the reaction was diluted to 30 mL with CH2Cl2 and washed with 10% sodium carbonate solution. The organic layers were dried (MgSO4), filtered and concentrated. The crude product was loaded onto a Biotage 12S column with dichloromethane and eluted with a step gradient of dichloromethane (150 mL), 2.5/97.5 MeOH/dichloromethane (150 mL) and 5/95 MeOH/dichloromethane (200 mL) to afford the desired product as a tan oil (14 mg, 100%).

Provenance & Evidence