Hydrochloric Acid → HCID 59146099, compound

Participants

Reaction Steps

To a suspension of ethyl 3-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoate (D166) (720 mg) in isopropanol (20 mL) was added 20% sodium hydroxide (1.52 g) solution, then the reaction mixture was stirred at room temperature overnight. The mixture was acidified with HCl (2 M) to pH 4. The solvent of the reaction was removed by evaporation. The residue was dissolved in DMF (5 mL). The precipitation was filtered and the filtrate was purified by Mass Directed Auto Prep to afford 3-[5-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-7-fluoro-1H-indol-2-yl]propanoic acid (E114) (41 mg) as a white solid. δH (DMSO-d6, 400 MHz): 1.32 (6H, s), 2.65 (2H, t), 2.94 (2H, t), 5.38 (1H, m), 6.38 (1H, s), 7.43 (1H, d), 8.01 (1H, s), 8.48 (1H, d), 8.85 (1H, d), 11.78 (1H, s); δF (DMSO-d6, 376 MHz): −132.6; MS (ES): C21H18ClFN4O4 requires 444. found 445.2 (M+H+).

Provenance & Evidence