1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2-Methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenylamino)-acetic acid ethyl ester

Participants

Reaction Steps

(2-Methyl-5-piperidin-3-yl-phenylamino)-acetic acid ethyl ester (Example 13-1; 63 mg, 0.23 mmol) was dissolved in 2 mL CH2Cl2 and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide (87 mg, 0.46 mmol) and 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylic acid (65 mg, 0.23 mmol) were added. The reaction was stirred at ambient temperature under nitrogen for 24 h. The reaction was flash chromatographed with 30% ethyl acetate/hexanes to yield 19 mg (15%) of the desired (2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenylamino)-acetic acid ethyl ester as a clear oil.

Provenance & Evidence