Diisopropylethylamine → 5-(4-Acetylpiperazin-1-yl)-N-((3-fluoro-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methyl)picolinamide

Participants

Reaction Steps

To a mixture of (3-fluoro-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 84-2 (54 mg, 0.20 mmol), 5-(4-acetylpiperazin-1-yl)picolinic acid 48-2 (50 mg, 0.20 mmol) and HATU (76 mg, 0.20 mmol) in DMF (0.9 mL) was added DIEA (0.16 mL, 1.00 mmol). The mixture was stirred at room temperature for 2 hours. The solvent was removed by rotary evaporation. The crude product was purified by reverse phase HPLC to give 5-(4-acetylpiperazin-1-yl)-N-((3-fluoro-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methyl)picolinamide 84 as a white powder. MS m/z 503.20 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 9.28 (t, 1H, J=6.4 Hz), 8.92 (d, 1H, J=5.2 Hz), 8.62 (m, 1H), 8.32 (m, 2H), 8.20 (d, 1H, J=4.8 Hz), 7.88-7.82 (m, 2H), 7.43 (dd, 1H, J1=9.0 Hz, J2=3.2 Hz), 4.59 (d, 2H, J=6.4 Hz), 3.61-3.58 (m, 4H), 3.41-3.39 (m, 4H), 2.05 (s, 3H).

Provenance & Evidence