Aniline → 2'-methyl-5'-(5-methyl-1,3,4-oxadiazol-2-yl)-N-phenyl-1,1'-biphenyl-4-carboxamide

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Reaction Steps

2′-Methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxylic acid (50 mg, 0.17 mmol), aniline (16 mg, 0.17 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (33 mg, 0.17 mmol) and DMF (20 drops) were suspended in dry DCM (5 ml) and stirred at room temperature under nitrogen for 4 h. The mixture was absorbed onto an SPE (silica, 10 g), eluted with DCM and then with a DCM/ethanol/ammonia gradient (250:8:1 to 100:8:1). The solvent was evaporated from the product fractions under vacuum to yield 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-N-phenyl-1,1′-biphenyl-4-carboxamide as a white solid (32 mg, 51%). NMR; δH [2H6]—DMSO 10.34,(1H, b), 8.06,(2H, d), 7.91,(1H, dd), 7.80,(3H, m), 7.57,(3H, m), 7.36,(2H, t), 7.11,(1H, t), 2.57,(3H, s), 2.34,(3H, s). LCMS; retention time 3.39 min, MH+ 370.

Provenance & Evidence