反应详情

温度

50 °C

4-(3-Chloro-4-fluorophenyl)-3-[4-(hydroxymethyl)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one (20 mg, 0.064 mmol) was dissolved in anhydrous EtOH (0.6 mL) followed by addition of 2 M of sodium hydroxide in water (60 μL). Reaction was stirred at 50° C. for 4 hrs. Consumption of starting material was monitored by TLC. The sample was quenched with acetic acid, diluted with MeOH and purified by preparative LCMS. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash silica column chromatography to yield the desired product (16 mg, 87%). 11-1 NMR (400 MHz, DMSO-d6) δ: 11.49 (s, 1H), 9.02 (s, 1H), 7.18 (dd, J=9.1, 9.1 Hz, 1H), 6.97 (dd, J=6.6, 2.7 Hz, 1H), 6.69 (m, 1H), 5.68 (t, J=6.2 Hz, 1H) 4.72 (d, J=5.8 Hz, 2H); MF=C10H8ClFN4O3; LCMS calculated for C10H9ClFN4O3(M+H)+: m/z=287.035.

1. customReaction
2. customConsumption of starting material
3. customThe sample was quenched with acetic acid
4. additiondiluted with MeOH
5. custompurified by preparative LCMS
6. additionThe reaction was diluted with water
7. extractionextracted with ethyl acetate three times
8. dry with materialdried with sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude residue was purified by flash silica column chromatography