Hydrochloric Acid → HCID 44548223, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cis-methyl-2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]cyclopropanecarboxylate (D65) (40 mg) in THF (5 mL) was added aqueous NaOH (2 M, 1 mL). The reaction was stirred at 60° C. for 4 h. The mixture was cooled to room temperature and acidified with aqueous HCl (2 M) to pH 4-5, partitioned between ethyl acetate (25 mL) and water (20 mL). The organic phase was washed with water (25 mL) and saturated 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 cis-2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]cyclopropanecarboxylic acid (E40) (20 mg). δH (DMSO-d6, 400 MHz): 1.31 (1H, m), 1.36 (6H, d), 1.43 (1H, m), 1.72 (1H, m), 2.45 (1H, m), 3.61 (3H, s), 4.88 (1H, m), 7.21 (2H, m), 7.46 (2H, m), 7.82 (1H, dd), 8.12 (1H, dd), 8.19 (1H, d), 12.28 (1H, br s). MS (ES): C24H22ClN3O4 requires 451; found 452.2 (M+H+).

Provenance & Evidence