Triethylamine → N-[1-(3,4-Dichloro-benzyl)-azetidin-3-ylmethyl]-2-(6-ethoxy-benzothiazol-2-ylsulfanyl)-acetamide

Participants

Reaction Steps

A solution of (6-Ethoxy-benzothiazol-2-ylsulfanyl)-acetic acid (0.087 g, 0.326 mmol) in dichloromethane (3 ml) is treated with triethylamine (0.041 ml, 0.326 mmol) and [(Benzotriazol-1-yloxy)-dimethylamino-methylene]-dimethyl-ammonium; tetrafluoro borate (0.104 g, 0.326 mmol) and stirred at ambient temperature for 3 minutes. To the reaction mixture is added a solution of C-[1-(3,4-Dichloro-benzyl)-azetidin-3-yl]-methylamine (0.08 g, 3.26 mmol) in dichloromethane (1 ml), with stirred for a further 3 hours. The reaction mixture is partitioned between ethyl acetate and sodium bicarbonate solution. The organic phase is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography using 95:5 dichloromethane:methanol as eluent to afford N-[1-(3,4-Dichloro-benzyl)-azetidin-3-ylmethyl]-2-(6-ethoxy-benzothiazol-2-ylsulfanyl)-acetamide. [MH]+ 495.8.

Provenance & Evidence