1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Phenyl-N-(5-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]-pyridin-2-YL)butyramide

Participants

Reaction Steps

To a solution of [4-(6-aminopyridin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)-methanone (0.035 g, 0.10 mmol) in dichloromethane was added diisopropylethylamine (0.084 mL, 0.48 mmol), followed by 1-hydroxybenzotriazole monohydrate (0.018 g, 0.12 mmol), EDCI (0.023 g, 0.12 mmol) and DMAP (0.015 g, 0.12 mmol). The resulting mixture was stirred for 15 minutes and 3-phenyl-1-propylamine (0.020 g, 0.12 mmol) was added. After stirring for 18 h, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification by preparative thin layer chromatography afforded the title compound as a pale white solid (6.2 mg, 12.5% yield). 1H NMR(300 MHz, CDCl3) δ 8.12, 7.97, 7.87, 7.72, 7.59, 7.34, 7.10-7.29, 3.98, 3.34, 3.22, 3.02, 2.70, 2.37, 2.08. MS (ES+) m/z 497.2 (M+1).

Provenance & Evidence