Hydrochloric Acid → HCID 59085882, compound

Participants

Reaction Conditions

Reaction Steps

Through a 0° C. solution of 0.221 g (0.485 mmol) ethyl(2-{(tert-butoxycarbonyl)[2,2-difluoro-2-(1-oxidopyridin-2-yl)ethyl]amino}-3-fluoropyridin-4-yl)acetate 30-1, contaminated with ethyl(2-{(tert-butoxycarbonyl)[2,2-difluoro-2-(1-oxidopyridin-2-yl)ethyl]amino}-3-fluoropyridin-4-yl)acetate, in 3 mL EtOAc was passed a steady stream of HCl gas for 20 min. The reaction was stirred at 0° C. for 20 min. The mixture was then flushed with N2 and poured onto 200 mL EtOAc/50 mL 2.0M NaOH/7 mL conc NaOH. The layers were mixed and then separated. The aqueous layer was back extracted with 25 mL EtOAc. The combined organics were washed w/100 mL water and 100 mL brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by automated flash chromatography (40 g silica cartridge, linear gradient 0-5% MeOH/CH2Cl2 over 30 min, 30 mL/min flow rate) provided ethyl(2-{[2,2-difluoro-2-(1-oxidopyridin-2-yl)ethyl]amino}-3-fluoropyridin-4-yl)acetate 30-2. 1H NMR (CDCl3, 400 MHz) δ8.288 (d, 1H, J=6.41 Hz, ArH); 7.727 (d, 1H, J=5.13 Hz, ArH); 7.622 (dd, 1H, J=2.20 Hz, 7.87 Hz, ArH); 7.363-7.323 (m, 1H, ArH); 7.297-7.257 (m, 1H, ArH); 6.455 (t, 1H, J=4.95 Hz, ArH); 4.751-4.663 (m, 2H, CH2); 4.164 (dd, 2H, J=7.14 Hz, 14.28 Hz, CH2); 3.560 (s, 2H, CH2); 1.254 (t, 3H, J=7.15 Hz, CH3); MS (Electrospray): m/z 356.1 (M+H).

Provenance & Evidence