[C:1](/[C:3](/[CH:6](OC)OC)=[CH:4]\[O-])#[N:2].[Na+].Cl.[S:13]1[CH:17]=[C:16]([NH2:18])[C:15]([NH2:19])=[CH:14]1>CO>[NH2:19][C:15]1[C:16]2=[N:18][CH:4]=[C:3]([C:1]#[N:2])[CH:6]=[C:17]2[S:13][CH:14]=1To a solution of sodium (E)-2-cyano-3,3-dimethoxyprop-1-en-1-olate (1012 mg, 6.13 mmol) in methanol (12 mL) was added concentrated hydrochloric acid (503 μL 6.13 mmol). The solution was stirred for 5 minutes, and then a solution of thiophene-3,4-diamine (700 mg, 6.13 mmol) in methanol (12 mL) was added. The solution was stirred at reflux for 3 hours, and then a solution of concentrated HCl (1.0 mL) in methanol (2 mL) was added. The reaction was stirred at reflux for an additional two hours, quenched with TEA (3 mL), and concentrated. The crude product was purified via silica gel chromatography, eluting with 0-100% ethyl acetate in heptanes, to provide the title compound (250 mg, 1.427 mmol). MS m/z=176 (M+H).
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