Diisopropylethylamine → 3-[5-(4-cyano-phenyl)-1,3,4-oxadiazol-2-ylmethyl]-N-((S)-6-morpholin-4-yl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-benzamide

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Reaction Steps

Add N,N-diisopropylethyl amine (0.17 mL, 0.95 mmol), 7-aza-hydroxybenzotriazole (0.040 g, 0.29 mmol) and EDC (0.06 g (0.31 mmol) to a solution of 3-[5-(4-cyano-phenyl)-[1,3,4]oxadiazol-2-ylmethyl]-benzoic acid (0.106 g, 0.24 mmol) in 3 mL of N,N-dimethylacetamide. Stir the mixture at room temperature for 1 h then add (S)-6-morpholin-4-yl-4,5,6,7-tetrahydro-benzothiazol-2-ylamine dihydrobromide (0.12 g, 0.30 mmol) in one portion and heat overnight at 60° C. Cool the reaction mixture to room temperature and dilute with H2O. Add an aqueous solution of sodium bicarbonate until the pH of the solution is alkaline causing a solid to precipitate from solution. Collect the solid by filtration, wash with H2O and dry on the filter pad. Purify the isolated material by preparative reverse phase HPLC to give 0.02 g, 13% yield of 3-[5-(4-cyano-phenyl)-1,3,4-oxadiazol-2-ylmethyl]-N—((S)-6-morpholin-4-yl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-benzamide as a white powder. MS, ES+ 527.67 (M+H), rt 1.24 min.

Provenance & Evidence