Triethylamine → 2-Methoxymethyl-thiazolo[5,4-b]pyridin-6-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)-amide

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Reaction Steps

A suspension of 1.03 g (4.62 mmol) of 2-methoxymethylthiazolo[5,4-b]pyridin-6-yl-carboxylic acid in 40 mL of methylene chloride was mixed with 1.6 g=1.0 mL (13.5 mmol) of thionyl chloride and refluxed for 90 minutes, during which time the solid gradually dissolved. After the liquid components had been distilled off, the crude product was taken up twice more in methylene chloride and concentrated again. The resulting crude acid chloride (1.2 g) was taken up in 40 mL of tetrahydrofuran, added dropwise to a mixture of 0.94 g (4.86 mmol) of N-(2-ethoxy-carbonylethyl)aniline and 2.1 mL (13.8 mmol) of triethylamine in 30 mL of tetrahydrofuran and stirred for 2 hours at room temperature. Then it was diluted with 200 mL of ethyl acetate, washed with 100 mL of 14% saline solution, and the organic phase was dried with sodium sulfate. After the solvent had been removed in vacuo, the crude product obtained was purified by flash chromatography (silica gel; methylene chloride/ethanol=100:1). Yield: 1.57 g (87% of theory)of yellow oil; Rf value: 0.55 (silica gel; methylene chloride/ethanol=19:1).

Provenance & Evidence