C1COCC1.Cl.[CH3:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[NH2:13].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[O:32][CH2:33][C:34]#[CH:35])[C:26](Cl)=[O:27]>O>[CH3:7][CH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[NH:13][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:31]([O:32][CH2:33][C:34]#[CH:35])=[C:23]([O:22][CH3:21])[CH:24]=1
To a mixture of 20 ml of THF, 0.50 g of 2-methylcyclopentylamine hydrochloride and 1.0 g of triethylamine was added 0.50 g of 3-methoxy-4-(2-propynyloxy)benzoyl chloride. The mixture obtained was stirred at room temperature for 3 hours. Then, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 235 mg of N-(2-methylcyclopentyl)-3-methoxy-4-(2-propynyloxy)benzamide (hereinafter, described as the compound 18 of the present invention) represented by the formula:
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