Diisopropylethylamine → Tert-butyl 4-(6-((3-fluoro-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methylcarbamoyl)pyridin-3-yl)piperazine-1-carboxylate

Participants

Reaction Steps

To a mixture of 5-(4-(tert-butoxycarbonyl)piperazin-1-yl)picolinic acid 49-4 (92 mg, 0.3 mmol), (3-fluoro-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 84-2 (81 mg, 0.3 mmol) and HATU (114 mg, 0.3 mmol) in DMF (1.5 mL) was added DIEA (0.15 mL, 0.9 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate (100 mL), washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, and eluted with 5% methanol in dichloromethane to give tert-butyl 4-(6-((3-fluoro-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methylcarbamoyl)pyridin-3-yl)piperazine-1-carboxylate 49-5 as a pale yellow oil. MS m/z 561.2 (M+1)

Provenance & Evidence