Diisopropylethylamine → HCID 59149726, compound

Participants

Reaction Conditions

Reaction Steps

DIPEA (0.321 mL, 1.94 mmol) was added to 2-[4-[4-hydroxy-1-[3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenoxy]acetic acid (283 mg, 0.65 mmol), N-(2-methoxyethyl)methylamine (63 mg, 0.71 mmol) and HATU (270 mg, 0.71 mmol) in DMF (5 mL) at 20° C. under nitrogen. The resulting solution was stirred at 20° C. for 4 hours. Water (50 mL) was then added and the mixture was extracted with DCM (2×50 mL). The combined organics were dried (Na2SO4), filtered and evaporated to give a orange oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane then 0 to 10% MeOH in EtOAc. Pure fractions were evaporated to dryness then tritutated with isohexane, filtered and dried to afford 2-[4-[4-hydroxy-1-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperidin-4-yl]phenoxy]-N-(2-methoxyethyl)-N-methylacetamide (161 mg, 48.9%) as a white solid.

Provenance & Evidence