Hydrochloric Acid → 6-{4-[({5-[(2-Fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-piperidin-1-yl}nicotinic acid

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Reaction Steps

A mixture of 2M NaOH (2 mL, 4 mmol) and methyl 6-{4-[({5-[(2-fluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]piperidin-1-yl}nicotinate (17 mg, 0.04 mmol) (Example 612) in MeOH (10 mL) was stirred for 16 h then taken to pH 7 by addition of 2M HCl. The solution was concentrated by evaporation to give a cloudy aqueous mixture that was cooled on an ice bath. The precipitate was collected by filtration, washed with water and Et2O and dried to give the title compound (13 mg, 88%) as a solid; 1H NMR (CD3OD) δ 8.61 (s, 1H), 8.02-7.88 (m, 2H), 7.16-7.05 (m, 2H), 7.05-6.97 (m, 1H), 6.75 (d, 1H), 4.47-4.37 (m, 2H), 4.17-4.06 (m, 1H), 3.08-2.97 (m, 2H), 1.99-1.89 (m, 2H), 1.63-1.50 (m, 2H); MS m/e MH+ 427.

Provenance & Evidence