[C:1](=[O:5])(OC)[NH2:2].N[C:7]1[S:11][C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=2[C:8]=1[C:16]#[N:17].[F:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]([NH:23][NH2:24])=O.C(N(CCC)CCC)CC>COCCO>[F:18][C:19]1[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=1[C:21]1[N:17]=[C:16]2[N:24]([C:1](=[O:5])[NH:2][C:7]3[S:11][C:10]4[CH2:12][CH2:13][CH2:14][CH2:15][C:9]=4[C:8]=32)[N:23]=1
The methyl carbamate of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo(b)thiophene (7.08 g), 2-fluorobenzhydrazide (4.66 g), 2-methoxyethanol (100 mL) and tri-n-propylamine (3 mL) are refluxed under nitrogen for 19 hours. The mixture is cooled and the precipitate collected. The mother liquor is treated with methanol (100 mL) and refrigerated 24 hours to produce a second crop of solid. The combined material is recrystallized from 2-methoxyethanol and dried 20 hours at 100°/0.01 mm to afford 2-(2-fluorophenyl)-8,9,10,11-tetrahydro[1]benzothieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)one, which decomposes above 316°. The yield is 50%.
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