CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:8]([CH3:16])=[C:9]([C:14]#[N:15])[S:10][C:11]=1[S:12][CH3:13])=O.[C:18]1([NH:24][C:25]([NH2:27])=[NH:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.CO>[CH3:16][C:8]1[C:7]([C:5]2[CH:4]=[CH:3][N:27]=[C:25]([NH:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:26]=2)=[C:11]([S:12][CH3:13])[S:10][C:9]=1[C:14]#[N:15]To a solution of 4-(3-dimethylamino-acryloyl)-3-methyl-5-methylsulfanyl-thiophene-2-carbonitrile (0.2 mmol) in acetonitrile (0.25 mL) was added N-phenyl guanidine (1 equivalent, 0.2 mmol) and the reaction heated at reflux for 24 hours. The resulting mixture was cooled to room temperature then diluted with methanol (3 mL). The resulting slurry was filterred washed with methanol to afford IIb-7.
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