Thionyl Chloride → 2-[2-(4-Cyanophenyl)ethyl]quinazolin-7-yl-carboxylic acid-n-phenyl-n-(2-methoxycarbonylethyl)amide

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Reaction Steps

0.4 g (1.3 mmol) of 2-[2-(4-cyanophenyl)ethyl]quinazoline-7-carboxylic acid and 5 mL of thionyl chloride were stirred for 60 minutes at 50° C. Then the thionyl chloride was distilled off, the residue was dissolved in methylene chloride, mixed with 0.24 g (1.3 mmol) of methyl 3-(N-phenylamino)propionate and 0.22 mL of (1.3 mmol) of N-ethyldiisopropylamine and stirred for 18 hours at ambient temperature. After evaporation of the solvent in vacuo, the residue was chromatographed on silica gel and eluted with methylene chloride containing 1% methanol. Yield: 230 mg (37% of theory); Rf value: 0.64 (silica gel, methylene chloride/methanol=9:1).

Provenance & Evidence