O-Phenylenediamine → N-(2-aminophenyl)-6-{[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}-1-benzothiophene-2-carboxamide

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To a solution of 6-{[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methyl}-1-benzothiophene-2-carboxylic acid (20 mg, 0.055 mmol) and 1,2-phenylenediamine (15 mg, 0.14 mmol) in 1 mL DMF was added 3-{[(ethylimino)-methylene]amino}-N,N-dimethylpropan-1-aminium chloride (16 mg, 0.082 mmol). The reaction was stirred at ambient temperature for 12 hours. Purification by reverse phase mplc gave the title compound as a white solid (TFA salt). 1H NMR (CD3OD) δ 8.19 (s, 1H), 8.00 (s, 1H), 7.96 (d, J=8.2 Hz, 1H), 7.93 (m, 2H), 7.48 (dd, J=8.2, 1.5 Hz, 1H), 7.37 (m, 1H), 7.32 (m, 1H), 7.24 (m, 2H), 7.07 (m, 2H), 4.48 (s, 2H), 3.86 (s, 3H). LC/MS (EI): cal'd 457.1 (MH+), exp 457.1 (MH+).

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