Hydrochloric Acid → HCID 44546701, compound

Participants

Reaction Steps

To a solution of ethyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]carbonyl}glycinate (D96) (50 mg) in THF (5 mL) was added aqueous NaOH (2 M, 2 mL). The reaction was stirred at room temperature overnight. The mixture was acidified with aqueous HCl (2 M) to pH 4-5, partitioned between ethyl acetate (25 mL) and water (25 mL). The organic phase was washed with water (25 mL) and brine (25 mL), dried over anhydrous sodium sulphate and evaporated to give the crude product, which was purified by Mass Directed Auto Prep to afford N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]carbonyl}glycine (E72) (28 mg). δH (DMSO-d6, 400 MHz): 1.36 (6H, d), 3.93 (2H, d), 4.90 (1H, m), 7.34 (1H, t), 7.47 (1H, d), 8.00 (1H, dd), 8.23 (2H, m), 8.42 (2H, m), 8.54 (1H, t), 11.55 (1H, s), 12.54 (1H, br s). MS (ES): C22H19ClN4O6 requires 454; found 455.2 (M+H+).

Provenance & Evidence