[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10](=[C:13](OC)[CH3:14])[C:11]#[N:12])=[N:7][C:6]=2[CH:17]=1.O.[NH2:19][NH2:20]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[C:13]([CH3:14])=[N:20][NH:19][C:11]=3[NH2:12])=[N:7][C:6]=2[CH:17]=1A suspension of 2-(5-fluorobenzothiazol-2-yl)-3-methoxybut-2-enenitrile (330 mg, 1.3 mmol) and hydrazine hydrate (70 μL) in methanol (40 mL) was heated to reflux overnight. The solution was then cooled to room temperature and the resulting solid was isolated by filtration. The crude material was recrystallized from ethanol to yield 260 mg (78%, 10% for five steps) of the title compound. MS (m/z, ES+): 249.0 (M+1, 100%).
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