Diisopropylethylamine → N-((2',3-dimethyl-2,4'-bipyridin-5-yl)methyl)-5-(pyrazin-2-yl)picolinamide

Participants

Reaction Steps

To a mixture of 5-(pyrazin-2-yl)picolinic acid 41-4 (20 mg, 0.1 mmol), (2′,3-dimethyl-2,4′-bipyridin-5-yl)methanamine 63-2 (21 mg, 0.1 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (38 mg, 0.1 mmol) in DMF (1.0 mL) was added DIEA (0.053 mL, 0.3 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted into DMSO and purified by HPLC to give N-((2′,3-dimethyl-2,4′-bipyridin-5-yl)methyl)-5-(pyrazin-2-yl)picolinamide 63 as white solid. MS m/z 397.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ 9.59 (t, 1H), 9.39 (d, 1H), 9.33 (d, 1H), 8.76 (m, 1H), 8.68 (m, 2H), 8.45 (d, 1H), 8.15 (d, 1H), 7.65 (d, 1H), 7.34 (b, 1H), 7.27 (d, 1H), 4.51 (d, 2H), 2.46 (s, 3H), 2.26 (s, 3H).

Provenance & Evidence