Hydrochloric Acid → HCID 44547323, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoate (D156) (120 mg) in isopropanol (25 mL) and water (5 mL) was added 0.5 mL of 20% aqueous NaOH solution. The reaction mixture was stirred at 20° C. overnight. Afterwards, the mixture was adjusted to pH 3 by addion of 6 M HCl and evaporated. The residue was treated with 6 mL DMF and filtered. The filtrate was purified by MDAP to give the designed product 3-[6-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-5-fluoro-1H-indol-3-yl]propanoic acid (E109) (45 mg). δH (DMSO-d6, 400 MHz): 1.30 (6H, d), 2.59 (2H, t), 2.88 (2H, t), 4.82 (1H, m), 7.37 (1H, s), 7.38 (1H, d), 7.48 (1H, d), 8.04 (1H, dd), 8.06 (1H, d), 8.12 (1H, d), 11.20 (1H, s); δF (DMSO-d6, 376 MHz): −121.5; MS (ES): C22H19ClFN3O4 requires 443.1; found 444.2 (M+H+).

Provenance & Evidence