Triethylamine → N-[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]-N'-[2-(5-isopropyl-1,2,4-oxadiazol-3-yl)ethyl]urea

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Reaction Steps

2-(5-Isopropyl-1,2,4-oxadiazol-3-yl)ethanamine (Amine 16) (129.2 mg; 0.48 mmol; 2 eq) is dissolved in DMF (4 ml). Triethylamine (133 μl; 0.96 mmol; 4 eq) and N-[2-(cyanomethyl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide (Intermediate 6) (79.3 mg; 0.24 mmol; 1 eq) are added. After less than 1 min the mixture becomes homogeneous, and after 30 min the reaction is complete. Solvents are evaporated and the resulting crude product is purified by preparative HPLC. The purified fractions are neutralized with NaHCO3 sat. solution and the desired product is extracted with DCM. The combined organic layers are dried over MgSO4, filtered and concentrated to Compound (82) as a white powder (29.6 mg; 30%).

Provenance & Evidence