Sodium Hydroxide → (1-{5-[({5-[(3,4-Difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridin-2-yl}piperidin-4-yl)acetic acid

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Reaction Steps

To a solution of methyl (1-{5-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridin-2-yl}piperidin-4-yl)acetate (Example 619, 189 mg, 0.40 mmol) in MeOH (10 mL) was added a 2M solution of NaOH (1 mL). The resulting yellow solution was allowed to stir at ambient temperature overnight. The volatile organics were removed by evaporation and residue adjusted to pH ˜1 with 2M HCl and the suspension was filtered and dried to leave a solid which was dissolved in DMSO/MeCN/water(7:2:1) and purified on a reverse phase preparative HPLC column eluting 5-95% MeCN 0.2% TFA. The title compound was isolated as a yellow solid (108 mg, 0.235 mmol; 58.9%); 1H NMR δ 1.16-1.27 (m, 2H), 1.76 (d, 2H), 1.91-1.99 (m, 1H), 2.19 (d, 2H), 2.90 (t, 2H), 4.21 (d, 2H), 7.00 (br d, 1H), 7.34-7.37 (m, 1H), 7.49 (q, 1H), 7.67-7.73 (m, 1H), 7.98 (d, 1H), 8.46 (s, 1H), 11.01 (s, 1H), 11.23 (s, 1H); CO2H not seen; MS m/e MH+ 459.

Provenance & Evidence