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0 °C

Methyl 4-(5-cyanopyridin-2-yl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperazine-2-carboxylate (130 mg, 0.3 mmol) was dissolved in MeOH (4 mL) and cooled to 0° C. 1N NaOH solution (0.3 mL) was added and the reaction mixture was slowly warmed to room temperature and stirred at 50° C. for 1 h. The MeOH was removed under reduced pressure and the aqueous layer was washed with EtOAc. The aqueous layer was acidified to pH 2-3 using 1.5N HCl, extracted with EtOAc, dried over anhydrous sodium sulfate and concentrated over reduced pressure. The crude product was purified by preparative TLC (eluent petroleum ether/EtOAc/AcOH 4:6:0.1 v/v) to get 4-(5-cyanopyridin-2-yl)-1-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)piperazine-2-carboxylic acid (30 mg, yield 24%). 1H NMR (400 MHz, DMSO-d6) δ 8.49-8.47 (m, 1H), 8.20-8.12 (m, 1H), 8.07 (br s, 1H), 7.89-7.83 (m, 1H), 7.75-7.71 (m, 2H), 6.91 (d, J=7.6 Hz, 1H), 5.00-4.89 (m, 1H), 4.72-4.54 (m, 1H), 4.33-4.23 (m, 1H), 3.62-3.47 (m, 2H), 3.17-3.12 (m, 2H). MS (ESI) m/z: Calculated for C21H15F3N6O4: 472.11. found: 473.2 (M+H)+.

1. temperaturethe reaction mixture was slowly warmed to room temperature
2. customThe MeOH was removed under reduced pressure
3. washthe aqueous layer was washed with EtOAc
4. extractionextracted with EtOAc
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated over reduced pressure
7. customThe crude product was purified by preparative TLC (eluent petroleum ether/EtOAc/AcOH 4:6:0.1 v/v)