[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC(CO[C:20]2[N:24]([CH3:25])[N:23]=[CH:22][C:21]=2[CH:26]=[O:27])=CC=1.C(N(CC)CC)C>CN(C)C=O>[CH3:25][N:24]1[C:20]([N:10]2[CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)=[C:21]([CH:26]=[O:27])[CH:22]=[N:23]1A mixture of 1-phenylpiperazine (3.40 g), 5-[(4-chlorobenzyl)oxy]-1-methyl-1H-pyrazol-4-carbaldehyde (600 mg), triethylamine (1.20 mL) and dimethylformamide (7.0 mL) was stirred at 120° C. for 8 hours, and then at a room temperature for 17 hours. Thereafter, the reaction solution was concentrated under a reduced pressure, and water was then added thereto. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous sodium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=80:20 to 10:90), so as to obtain the title compound (669 mg) in the form of a light yellow solid.
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