1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68516932, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL round-bottomed flask was charged with 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (0.0840 g, 0.358 mmol obtained from Example 19, step C), EDCI (0.0687 g, 0.358 mmol), HOBT (0.0549 g, 0.358 mmol), and DMF (5 mL). The reaction mixture was stirred for 30 minute and tert-butyl 4-(4-(1-(4-methoxybenzyl)-4-(4-amino-2-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (0.110 g, 0.179 mmol) and Hunig's base (0.0463 g, 0.358 mmol) were added. The reaction mixture was stirred for 18 hours, then diluted with water and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude material was purified by preparative TLC (0.5 mm thickness) eluting with CHCl3/MeOH(NH3 7N) 4:1. To the isolated product was added TFA (2 mL) and the solution was heated to 70° C. for 1 hour. The solution was concentrated and triturated with DCM/MeOH 1:1. The solids were collected by filtration to provide 5.1 mg (5%) of the desired product. LRMS M+1 (610.0) observed.

Provenance & Evidence