Dimethylformamide → N-(3-cyanophenyl)-2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-4-biphenylcarboxamide

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2′-Methyl-5′-(5methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (100 mg, 0.34 mmol), oxalyl chloride (0.03 ml, 0.41 mmol), and DMF (1 drop) were mixed in DCM (5 ml) and stirred at room temperature for 35 min. 3-Cyanoaniline (44 mg, 0.374 mmol) was added to the solution and the mixture stirred for 2 h; DMF (1 ml) was added and stirring continued for 18 h. The solvents were evaporated from the reaction under vacuum and the residue chromatographed on an SPE (silica, 5 g), eluting with DCM and then DCM/ethanol/ammonia (300:8:1). The product fractions were concentrated in vacuo to give N-(3-cyanophenyl)-2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide as a white solid (11 mg, 8%). NMR; δH [2H6]—DMSO 10.65,(1H, b), 8.28,(1H, m), 8.07,(3H, m), 7.91,(1H, dd), 7.79,(1H, d), 7.62-7.56,(5H, m), 2.57,(3H, s), 2.33,(3H, s). LCMS; retention time 3.49 min, MH+ 395

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