Triethylamine → HCID 67089053, compound

Participants

Reaction Steps

A mixture of 6-chloro-2-fluoro-3-(propylsulfonamido)benzoic acid (0.446 g, 1.51 mmol), EDCI (0.723 g, 3.77 mmol), and HOBt (0.578 g, 3.77 mmol) in DMF (6 mL) was stirred at room temperature for 25 minutes. tert-Butyl 5-amino-3-ethoxy-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (0.21 g, 0.755 mmol) was added to the reaction mixture, followed by the addition of Et3N (0.53 mL, 3.77 mmol). After stirring for 4 hours, the reaction mixture was diluted with EtOAc, washed with saturated aqueous NH4Cl, saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give the crude material. The crude material was purified by silica gel flash column chromatography (10% MeOH in CH2Cl2) to afford tert-butyl 5-(6-chloro-2-fluoro-3-(propylsulfonamido)benzamido)-3-ethoxy-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (90 mg, 22% yield).

Provenance & Evidence