[CH2:1]([O:3][CH:4](OCC)[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([F:17])[CH:8]=1)=O)[CH3:2].[NH2:21][NH:22][C:23]([NH2:25])=[S:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CI>C(O)C>[CH2:1]([O:3][CH:4]1[C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([F:17])[CH:8]=2)=[N:21][NH:22][C:23](=[S:24])[NH:25]1)[CH3:2]
A mixture of methyl 4-(diethoxyacetyl)-2-fluorobenzoate (0.63 g, 0.0022 mol), thiosemicarbazide (0.24 g, 0.0026 mol), and p-toluenesulfonic acid monohydrate (20 mg) in ethanol (6 mL) was heated at 90° C. for 1.5 h. After cooling to RT, to the mixture was added methyl iodide (0.7 mL, 0.01 mol). The mixture was stirred at RT for 1 h. The mixture was concentrated. The residue was dissolved in acetic acid (4 mL), and heated at 60° C. for 2 h. After cooling, the reaction mixture was concentrated. The residue was treated with methanol. The formed precipitate was collected by filtration, and dried in-vacuo to afford the desired product (180 mg). Analytical LCMS: (M+H)+=280.0.
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