Formic Acid → 4-(3-Chloro-phenyl)-2-[6-(3-hydroxy-propoxy)-5-methoxy-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide

Participants

Reaction Steps

A mixture of 0.200 g (0.42 mmole) of 4-(3-chloro-phenyl)-2-[5-(3-hydroxy-propoxy)-4-methoxy-2-nitro-phenylamino]-thiazole-5-carboxylic acid amide (VI.42), 0.150 g of 10% palladium on carbon catalyst, and 4 mL of 96% formic acid was stirred under 1 atmosphere of hydrogen at room temperature for 16 hours. The mixture was filtered through Diatomaceous earth, and the Diatomaceous earth pad was washed with formic acid. The filtrate was heated at reflux for 1 hour, cooled and concentrated under reduced pressure. The residue was dissolved in 4 mL of dimethylsulfoxide and 0.30 g of potassium hydroxide in 1 mL of water was added dropwise. The mixture was stirred at room temperature for 1 hour and then diluted with 10 mL of water. The resulting precipitate was collected by filtration and washed with water to give 0.105 g of 4-(3-chloro-phenyl)-2-[6-(3-hydroxy-propoxy)-5-methoxy-benzoimidazol-1-yl]-thiazole-5-carboxylic acid amide (I.42a) as a purple solid.

Provenance & Evidence