Water → HCID 90011212, compound

Participants

Reaction Conditions

Reaction Steps

Step-2: 5-6-(3-(4-Methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)nicotinic acid: In a sealed tube containing a solution of 6-(3-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-1H-pyrazol-1-yl)nicotinonitrile (0.80 g, 2.37 mmol) in methanesulfonic acid (5 mL, 77 mmol) and water (4 mL) was heated at 70° C. for 6 h. The reaction mixture was then cooled to room temperature and water (10 mL) was added to the above mixture followed by ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (30 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 500 mg (60%) of the title compound as white solid. 1HNMR (400 MHz, DMSO-d6) δ 13.71 (s, 1H, D2O exchangeable), 9.01 (d, J=2.5 Hz, 1H), 8.55 (dd, J=2.5 & 8.5 Hz, 1H), 8.06 (d, J=8.5 Hz, 1H), 7.80 (s, 1H), 3.40 (s, 3H); ESI-MS (m/z) 356 (MH)+.

Provenance & Evidence