Triethylamine → HCID 24958733, compound

Participants

Reaction Steps

To a solution of (2-cyano-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrol-1-yl)acetic acid (95 mg, 0.2 mmol, 1 equiv.) and triethylamine (0.16 mL, 1.2 mmol, 6 equiv.) in 2 mL of DMF was added ammonium chloride (67 mg, 1.2 mmol, 6 equiv.) followed by PyBOP (113 mg, 0.22 mmol, 1.1 equiv.) After stirring overnight, the reaction was then filtered into an HPLC vial and purified by reverse phase HPLC (15-95% CH3CN/water+0.1% TFA). The desired fractions were combined and the CH3CN was removed. The aqueous was basified with saturated aqueous sodium bicarbonate and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 50 mg (53%) of the title compound as a yellow foam. MS m/z 458.22 (MH+).

Provenance & Evidence