Diisopropylethylamine → 3-(4-Fluorophenyl)-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-2-oxo-2H-1,2'-bipyridine-5-carboxamide

Participants

Reaction Steps

To a solution of 3-(4-fluorophenyl)-2-oxo-2H-1,2′-bipyridine-5-carboxylic acid (20.0 mg, 0.05 mmol) in DMF (0.5 mL) were added hydrochloride salt of (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine (13.6 mg, 0.07 mmol), HATU (0.5 M in DMF; 0.16 mL, 0.08 mml) and diisopropylethylamine (36 μL, 0.21 mmol). The mixture was stirred at ambient temperature. After 30 min, the mixture was purified by reverse chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) to give the title compound (20 mg). HRMS 420.1470 (M+1). 1H NMR (400 MHz, CDCl3): δ 8.62 (d, J=4.8 Hz, 1H); 8.53 (d, J=2.5 Hz, 1H); 7.94-7.83 (m, 3H); 7.70 (dd, J=8.3, 5.4 Hz, 2H); 7.41 (t, J=5.8 Hz, 1H); 7.12 (t, J=8.5 Hz, 2H); 6.66 (d, J=7.7 Hz, 1H); 5.60-5.51 (m, 1H); 2.40 (s, 3H); 1.69 (d, J=7.1 Hz, 3H).

Provenance & Evidence