[NH2:1]C1SC(C)=NN=1.C(O[C:13]1[C:21](OC)=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][C:14]=1OC)CCC.C(N(C(C)C)CC)(C)C.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:17]([NH2:1])(=[O:18])[C:16]1[CH:20]=[CH:21][CH:13]=[CH:14][CH:15]=1
A compound represented by Formula 110, that is, 2-amino-5-methyl-1,3,4-thiadiazole (314.6 mg, 2.73 mmol, purchased from TCI Co.) was slowly added to 4-n-butoxy-3,5-dimethoxybenzoic acid represented by Formula 90 (772 mg, 3.04 mmol) prepared in Preparative Example 2 and diisopropylethylamine (1.64 mL, 10.92 mmol) in DMF (15 mL) at room temperature. After cooling the reaction mixture to 0° C. and adding 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate methanaminium (HATU, 1.15 g, 3.04 mmol) thereto, the mixture was agitated at room temperature for 24 hours. The reaction solvent was removed under reduced pressure and chloroform (30 mL) was added to the remaining concentrate to prepare a solution. The solution was washed with a potassium carbonate solution, followed by separation to form an organic layer. After drying the organic layer with sodium sulfate (Na2SO4), the solvent was removed again under reduced pressure. The obtained vacuum-concentrated mixture was subjected to separation and purification through column chromatography (ethyl acetate/hexane/triethylamine, 2:1:0.1, v/v/v) using silica gel (SiO2), resulting in a benzamide compound represented by Formula 24 as a desired product (VVZ-025; 545.7 mg, 56.8% yield).
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