Acetic Acid → 1-{[3-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]methyl}-3 azetidinecarboxylic acid

Participants

Reaction Steps

To a solution of 5-[3-(2-ethyl-3-formylphenyl)-1,2,4-thiadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile (D46) (110 mg) in dichloromethane (DCM) (5 mL) and methanol (5.00 mL) was added 3-azetidinecarboxylic acid (147 mg) and acetic acid (0.050 mL). The resulting solution was stirred at room temperature for overnight. Sodium triacetoxyborohydride (185 mg) was added and the reaction solution was stirred for 2 h. The solvent was removed in vacuo and the residue was purified by Mass Directed AutoPrep to give 1-{[3-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-thiadiazol-3-yl)-2-ethylphenyl]methyl}-3 azetidinecarboxylic acid (E17) (37 mg) as a TFA salt (white solid). δH (DMSO-d6, 400 MHz): 1.03 (3H, t), 1.31 (6H, d), 2.93 (2H, q), 3.60 (1H, m), 4.22 (4H, m), 4.52 (2H, s), 4.89 (1H, m), 7.38 (1H, t), 7.42 (1H, d), 7.51 (1H, s br), 7.82 (1H, d), 8.27 (1H, dd), 8.42 (1H, d), 10.20 (1H, s br), 13.13 (1H, br s). δF (DMSO-d6, 376 MHz): −73.7. MS (ES): C26H26N4O3S requires 462. found 463.2 (M+H+).

Provenance & Evidence