Hydrochloric Acid → HCID 178520528, compound

Participants

Reaction Steps

In a 3-neck 50 mL round-bottomed flask, (Z)-3-(5-(3,5-bis(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)acrylic acid (2) (0.065 g, 1 eq.), 3,3-difluoroazetidine HCl (0.028 g, 1.2 eq.) and EDC. HCl (0.042 g, 1.2 eq.) was dissolved in dichloromethane (5 mL). DIPEA (0.028 g, 1.2 eq.) was added at −5° C. followed by HOBt (0.033 g, 1.2 eq.) added at same temperature. Reaction was maintained at this temp for 1 h. Reaction completion was monitored on TLC using MeOH: dichloromethane (0.5:9.5) as mobile phase. The reaction mixture was quenched into the ice-water slurry (50 mL) and was extracted with ethyl acetate (3×20 mL). Organic layer was washed with brine solution (3×25 mL). The organic layer was dried using anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide the 0.80 g crude compound which was purified by column chromatography using ethylacetate and hexane as mobile phase. Product was eluted in 35% ethylacetate in hexane to afford 0.055 g (78%) title compound.

Provenance & Evidence