Trifluoroacetic acid → HCID 46927295, compound

Participants

Reaction Steps

A mixture of tert-butyl 2-(2′-methyl-3-(trifluoromethyl)-2,4′-bipyridin-5-yl)acetate 189-4 (230 mg, 0.65 mmol) and TFA (1 mL) in DCM (5 mL) was stirred at room temperature for 5 hours. The solvents were evaporated to dryness under high vacuum. The crude product, 2-(2′-methyl-3-(trifluoromethyl)-2,4′-bipyridin-5-yl)acetic acid 189-5, was dissolved in DMF (4 mL). 1-(4-(6-aminopyridin-3-yl)piperazin-1-yl)ethanone (173 mg, 0.78 mmol) and DIEA (910 uL, 5.22 mmol) were added to the solution before O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (372 mg, 0.98 mmol). The mixture was stirred at room temperature overnight. The solvent was removed by rotary evaporation. The crude product was purified by reverse phase HPLC to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(2′-methyl-3-(trifluoromethyl)-2,4′-bipyridin-5-yl)acetamide 189. MS m/z 499.2 (M+1); 1H NMR 400 MHz (MeOD) δ 8.78(s, 1H), 8.48(d, 1H), 8.26(s, 1H), 7.99(s, 1H), 7.88(d, 1H), 7.42-7.36(m, 2H), 7.31(d, 1H), 3.92(s, 2H), 3.69(t, 2H), 3.65(t, 2H), 3.16(t, 2H), 3.11(t, 2H), 2.57(s, 3H), 2.09(s, 3H).

Provenance & Evidence