Diisopropylethylamine → (S)-N'-(6-Chloropyridazin-3-yl)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzohydrazide

Beteiligte Stoffe

Reaktionsschritte

(S)-4-(5,5-Dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoic acid (400 mg, 1.285 mmol) was dissolved in DMF (2.57 mL) at room temperature. To the reaction mixture, was successively added N-ethyl-N-isopropylpropan-2-amine (670 μL, 3.85 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (489 mg, 1.285 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) and 3-chloro-6-hydrazinylpyridazine (186 mg, 1.285 mmol). The vial was sealed and immersed in a 55° C. oil bath. After stirring overnight, LC-MS indicated complete conversion to the product. After cooling to room temperature, the reaction mixture was transferred to water in a flask in an ice/water bath. The solution was extracted w with DCM (3×50 mL). The combined organic layers were then washed with water (2×50 mL) and brine (50 mL). The organic layer was dried over Na2SO4. The solution was then filtered and concentrated under reduced pressure to give the product as a yellow solid. The product thus obtained was was used in the next step without further purification. m/z (ESI) 438.0 (M+H)+.

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