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1-benzylpyrrolidine-3-amine represented by Formula 102 (180 mg, 1.02 mmol) was slowly added to a solution of 4-benzyloxy-3,4-dimethoxybenzoic acid represented by Formula 89 (323.88 mg, 1.12 mmol) prepared in Preparative Example 1 as well as diisopropylamine (0.71 mL, 4.09 mmol) in DMF (7 mL) at room temperature. The reaction mixture was cooled to 0° C. and, after adding 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate methanaminium (HATU, 388.29 mg, 1.02 mmol) thereto, the mixture was agitated at room temperature for 24 hours. After removing the reaction solvent under reduced pressure, chloroform (20 mL) was added to the remaining concentrate to form a solution, the solution was washed with a potassium carbonate solution, followed by separation to form an organic layer. The organic layer was dried with sodium sulfate (Na2SO4) and 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 12 as a desired product (VVZ-013; 392.9 mg, 86% yield).

1. customAfter removing the reaction solvent under reduced pressure, chloroform (20 mL)
2. additionwas added to the
3. concentrationremaining concentrate
4. customto form a solution
5. washthe solution was washed with a potassium carbonate solution
6. customfollowed by separation
7. customto form an organic layer
8. dry with materialThe organic layer was dried with sodium sulfate (Na2SO4)
9. customthe solvent was removed again under reduced pressure
10. concentrationThe obtained vacuum-concentrated mixture
11. customwas subjected to separation and purification through column chromatography (ethyl acetate/hexane/triethylamine, 2:1:0.1, v/v/v)