Benzoyl chloride, 3-chloro- → 3-[3-(3-Chloro-benzoylamino)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

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Reaction Steps

To a solution of 3-(3-amino-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (35.4 mg, 0.108 mmol) (from Example 3 supra) in THF (3 mL) were added diisopropylethyl-amine (28 mg, 0.216 mmol) (Aldrich) and then 3-chlorobenzoyl chloride (28 mg, 0.161 mmol) (Aldrich). The reaction was stirred at room temperature for 20 minutes before it was concentrated to remove the solvent. The residue was diluted with EtOAc (40 mL), washed with aqueous 1N NaOH (10 mL), brine (2×10 mL), dried (Na2SO4) and concentrated. The residue was purified by column chromatography (hexanes/EtOAc, 75/25 to 50/50) to give 3-[3-(3-chloro-benzoylamino)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 38.2 mg, 75.7%).

Provenance & Evidence