Hydrochloric Acid → HCID 23000569, compound

Participants

Reaction Steps

To a solution of 0.5 g (1.26 mmol) ethyl(5-chloro-2-{[2,2-difluoro-2-(2-pyridinyl)ethyl]amino}-3-fluoro-4-pyridinyl)acetate 1-5 in 5 mL MeOH was added 1.4 mL (1.4 mmol, 1M aqueous solution) LiOH and the reaction mixture allowed to stir 16 hours at room temperature, then 0.1 mL (0.1 mmol) more LiOH was added and the mixture heated to 45° C. for 1 hour, then cooled. To this was added 0.12 mL (1.45 mmol, 12M solution) HCl and the mixture concentrated to give (5-chloro-2-{[2,2-difluoro-2-(2-pyridinyl)ethyl]amino}-3-fluoro-4-pyridinyl)acetic acid 1-6 (mixed with LiCl). 1H NMR (400 mHz, CD3OD) δ8.60 (br d, 1H, J=4.77 Hz); 7.89 (ddd, 1H, J=7.7, 7.7, and 1.65 Hz); 7.70 (s, 1H); 7.67 (br d, 1H, J=7.87 Hz); 7.46 (dd, 1H, J=4.94 and 7.69 Hz); 4.32 (t, 2H, J=13 Hz); 3.72 (d, 2H, J=1.83 Hz);

Provenance & Evidence