Acetic Acid → HCID 44546700, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanal (D92) (100 mg), N-methylglycine (43 mg) and acetic acid (0.1 mL) in DCM (15 mL) was added sodium triacetoxyborohydride (103 mg). The reaction was stirred at 40° C. for 3 h. The mixture was cooled to room temperature and partitioned between DCM (25 mL) and water (25 mL). The organic phase was washed with water (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-{3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propyl}-N-methylglycine (E71) (80 mg, TFA salt). δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 2.08 (2H, m), 2.80 (2H, t), 2.82 (3H, s), 3.18 (2H, t), 4.07 (2H, s), 4.89 (1H, m), 7.23 (1H, t), 7.33 (1H, t), 7.45 (1H, d), 7.84 (1H, d), 7.96 (1H, d), 8.36 (1H, d), 10.87 (1H, s). MS (ES): C26H27ClN4O4 requires 482; found 483.2 (M+H+).

Provenance & Evidence