Anisamide Derivatives

US Patent 6,706,763 (March 16, 2004) Assignee Kyorin Pharmaceutical Company Utility Treatment of Metabolic Diseases 

A suspension of 17.2 g 2-methoxy-5-nitrobenzoic acid in 35 ml CH2CI2 was added to 35 ml oxalyl chloride with 1 drop DMAc and stirred for 1 hour at ambient temperature. The solvent was removed, 150 ml DMF, 15 ml TEA, and 16.9 g 4-trifluoromethylbenzylamine added, the mixture stirred for 2 hours at ambient temperature, poured into water, and product extracted with EtOAc. The residue was recrystallized from hexane/EtOAc and the product isolated, mp = 108-109 °C. Elemental analysis data supplied. 

The product from Step 1 (26.6 g) was dissolved in 270 ml EtOAc and hydrogenated using 2.6 g 10% palladium on carbon in a hydrogen atmosphere at ambient temperature for 

8 hours. The mixture was filtered through eelite, purified by eolumn ehromatography on silica gel using EtOAc, and 24.5 g of product isolated, mp = 115-117 °C. Elemental analysis data supplied. 

5-(2-Brom-2-carbamoylethyl)-2-methoxy-N-(4-trifluoro-methylbenzyl)benzamide 

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