[C:1]([OH:8])(=O)[C:2]#[C:3][CH2:4][CH2:5][CH3:6].[CH:9]1([NH2:12])[CH2:11][CH2:10]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl>ClCCl>[CH:9]1([NH:12][C:1](=[O:8])[C:2]#[C:3][CH2:4][CH2:5][CH3:6])[CH2:11][CH2:10]1A solution of 2-hexynoic acid (5.03 g) and cyclopropylamine (2.70 g) in dichloromethane (75 ml), and a solution of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (9.00 g) and 1-hydroxybenzotriazole hydrate (7.19 g) in dichloromethane (75 ml) were mixed, and the mixture was stirred at room temperature for 18 hr. 1N Hydrochloric acid (200 ml) was added, and the mixture was extracted with dichloromethane. The organic layer was washed with 5% aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and purified by silica gel column to give the title compound (6.04 g, 89%).
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