Hydrochloric Acid → HCID 44546860, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl ({3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propyl}oxy)acetate (D105) (80 mg) in THF (10 mL) was added NaOH (2 M, 2 mL). The reaction was stirred at 20° C. for 3 h. 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 ({3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]propyl}oxy)acetic acid (E80) (50 mg). δH (DMSO-d6, 400 MHz): 1.35 (6H, d), 1.89 (2H, m), 2.49 (2H, t), 3.52 (2H, t), 3.63 (3H, s), 4.01 (2H, s), 4.87 (1H, m), 7.17 (2H, m), 7.42 (2H, m), 7.77 (1H, dd), 8.12 (1H, dd), 8.19 (1H, d), 12.56 (1H, br s). MS (ES): C25H26ClN3O5 requires 483; found 484.2 (M+H+).

Provenance & Evidence