Hydrochloric Acid → (4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylcarbamoyl)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid

Participants

Reaction Conditions

Reaction Steps

To 60 mg (0.1 mmol), (4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylcarbamoyl)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester in THF/H2O (10 mL; 4:1), 5 mL (4M) aqueous Lithium Hydroxide solution was added and the mixture stirred at 60° C. for 5 hours. Acidified with concentrated hydrochloric acid which precipitated the desired compound. Filtered and dried under vacuum to afford (4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylcarbamoyl)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid, which was subsequently dissolved in methanol (5 mL) one equivalent of potassium hydroxide and 2 mL of H2O were added and the resulting mixture was stirred at 40 C for 2 hours. Evaporated to dryness to afford (4-{4-[5-(6-Trifluoromethyl-pyridin-3-ylcarbamoyl)-pyridin-2-yl]-phenyl}-cyclohexyl)-acetic acid as the potassium salt: M+1=484.1. HRMS=484.1822. 1H NMR (400 MHz, MeOD) δ ppm 0.79 (d, J=7.33 Hz, 1H) 1.11 (td, J=12.44, 2.91 Hz, 3H) 1.43-1.55 (m, 2H) 1.67-1.78 (m, J=7.14, 7.14, 6.95, 6.57 Hz, 2H) 1.79-1.89 (m, 3H) 2.02 (d, J=7.33 Hz, 2H) 2.14 (t, J=7.33 Hz, 1H) 2.47 (s, 1H) 7.29 (d, J=8.34 Hz, 2H) 7.75 (d, J=8.59 Hz, 1H) 7.88-7.95 (m, 2H) 8.31 (dd, J=8.46, 2.40 Hz, 1H) 8.43 (dd, J=8.46, 2.15 Hz, 1H) 8.97 (d, J=2.27 Hz, 1H) 9.08 (d, J=1.52 Hz, 1H)

Provenance & Evidence