Triethylamine → HCID 178522641, compound

Participants

Reaction Steps

To a solution of 3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinic acid (30 mg, 0.08 mmol, EXAMPLE 34 Step 3) in dichloromethane (1 mL) were added oxalyl chloride (33 microL, 0.38 mmol) and a catalytic amount of N,N-dimethylformamide at room temperature. After being stirred at room temperature for 30 min, the volatile was removed under reduced pressure. The resulting residue was dissolved in toluene (1 mL). Triethyl amine (10 microL, 0.08 mmol) and 4H-1,2,4-triazol-3-amine (8 mg, 0.09 mmol) were added to the mixture. After being refluxed for 15 h, the volatile was removed by evaporation. The residual material was dissolved in dichloromethane. The organic layer was washed with aq. sodium bicarbonate and concentrated in vacuo to afford the title compound as a brown oil. The crude product was purified by preparative HPLC.

Provenance & Evidence