Sodium Chloride → HCID 44176604, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of 1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)-phenyl)-1H-imidazole-4-carbohydrazide (192 mg, 0.383 mmol) in 1 mL pyridine was added acetic anhydride (0.085 mL, 0.767 mmol). The ice bath was removed and the reaction stirred for 1 h. The solvent was removed in vacuo and approximately 3 mL of PPA was added to the flask. The reaction was heated to 120° C. for 2 h. Upon completion of the reaction 10 mL ice water was added to the reaction. The mixture was transferred to a 150 mL Erlenmeyer flask and neutralized with 2M Na2CO3. Solid NaCl was added the solution was extracted with ethyl acetate 3×20 mL. The combined organic layers were dried with MgSO4 and the solvent was removed in vacuo. The residue was absorbed onto silica and purified by column chromatography using hexanes:ethyl acetate as eluents to afford 2-methyl-5-(1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)-1,3,4-oxadiazole (25 mgs, 13%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 8.53 (s, 1H), 8.15-8.14 (m, 1H), 8.05-8.02 (m, 1H), 7.93-7.90 (m, 1H), 7.88-7.83 (m, 3H), 7.75-7.71 (m, 3H), 7.69-7.66 (m, 1H), 7.41 (d, J=8.58 Hz, 2H), 3.28 (s, 3H), 2.58 (s, 3H); MS (ES): 525.0 [M+H]+ and 547.3 [M+Na]+.

Provenance & Evidence