1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57664898, compound

Participants

Reaction Steps

5-(Chloromethyl)-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxylic acid (103 mg, 0.334 mmol) obtained in Example 104b), HOBt (23 mg, 0.167 mmol, 0.5 eq.) and cyclopropylamine (0.031 ml, 0.434 mmol, 1.3 eq.) were dissolved in acetonitrile-DMF (2:1, 1.5 ml), WSC (78.4 mg, 0.401 mmol, 1.2 eq.) was added, and the mixture was stirred at room temperature for 2.5 hr. water (10 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate (30 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution, washed with 10% aqueous ammonium chloride solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated to give a white powder. This was subjected to column chromatography (elution solvent, ethyl acetate-hexane=2:3-3:2) on silica gel (manufactured by E. Merck, Art.7734, 10 g). The fraction obtained by elution with ethyl acetate-hexane (1:1-3:2) was concentrated, and diethyl ether was added to the residue. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (76 mg, 0.219 mmol, 65.4%).

Provenance & Evidence