1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

Participants

Reaction Steps

To a suspension of 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid (885 mg, 3.25 mmol, 1.00 equiv) in DMF (32 ml) at room temperature, {[2-(trifluoromethyl)phenyl]methyl}amine (456 μL, 3.25 mmol, 1.00 equiv), EDCI (748 mg, 3.90 mmol, 1.20 equiv), HOBT (527 mg, 3.90 mmol, 1.00 equiv), and diisopropylethylamine (DIEA, 2.80 ml, 16.3 mmol, 5.00 equiv) were added. Stirring was continued overnight at room temperature. The reaction mixture was partitioned between 1:1 water and ethyl acetate (200 ml). The product was extracted three times with ethyl acetate (50 ml). The ethyl acetate extracts were combined and washed successively with saturated ammonium chloride (100 ml), water (100 ml), and saturated sodium chloride (100 ml). The ethyl acetate solution was dried with Na2SO4, filtered, and concentrated under reduced pressure to yield 1.23 g (88%) of the title compound. MS ES+): m/e 428.7 [M+H]+.

Provenance & Evidence