Triethylamine → N-[5-[2-[(2E)-2-amino-2-hydroxyiminoethyl]-1,3-thiazol-4-yl]-4-methyl-1,3-thiazol-2-yl]acetamide

Participants

Reaction Conditions

Reaction Steps

N-[2-(cyanomethyl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]acetamide, Compound (3) (50 mg; 0.18 mmol; 1 eq.), is dissolved in dioxane (10 ml). Hydroxylamine hydrochloride (15 mg; 0.22 mmol; 1.20 eq.) and N,N-diethylethanamine (0.03 ml; 0.22 mmol; 1.20 eq.) are added and reaction mixture is heated at 80° C. overnight. Reaction mixture is cooled down and dioxane evaporated. The residue is taken up in EtOAc and washed several times with water (3×10 mL). The organic phases are dried over MgSO4, filtrated and evaporated. Crude material is purified by flash chromatography on silica gel (cyclohexane/ethylacetate, 50/50), affording the title compound as an oil (50 mg; 95%).

Provenance & Evidence