Hydrochloric Acid → Ethyl 3-((6-(4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)phenyl)-3-nitro-5-phenylpyridin-2-yl)amino)propanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(6-chloro-5-nitro-3-phenylpyridin-2-yl)phenyl)cyclobutyl)carbamate (1.03 g, 2.14 mmol) in EtOH (8 ml) was added triethylamine (1.49 ml, 10.72 mmol) and ethyl 3-aminopropanoate.HCl (1.65 g, 10.72 mmol) under nitrogen. The resulting mixture was stirred for 1.5 hours at 80° C. under microwave irradiation. Water was added and the mixture was extracted with AcOEt (3×15 ml). The combined organic phases were dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 30% EtOAc in cyclohexane) to give the title compound (1.2 g, quantitative). 1H NMR (500 MHz, CDCl3): 8.50 (1H, s), 8.38 (1H, s), 7.32 (2H, d), 7.23-7.18 (5H, m), 7.09-7.07 (2H, m), 5.00 (1H, br s), 4.12 (2H, q), 3.98 (2H, q), 2.71-2.68 (2H, t), 2.52-2.20 (4H, m), 2.00-1.95 (1H, m), 1.79-1.65 (1H, m), 1.40-1.10 (9H, br), 1.20 (3H, t).

Provenance & Evidence