Hydrochloric Acid → 1-[2-(3-{5-[3-Cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-4-piperidinecarboxylic acid

Participants

Reaction Steps

To a solution of ethyl 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-4-piperidinecarboxylate (D33) (64 mg) in isopropanol (3 mL) and water (3 mL) was added sodium hydroxide (50 mg). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was neutralized with 1 M HCl solution. The solvent was removed in vacuo. The residue was dissolved in THF, and filtered. The filtrate was purified by Mass Directed AutoPrep to give 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,3,4-thiadiazol-2-yl}-2-ethylphenyl)ethyl]-4-piperidinecarboxylic acid (E11) (15 mg) as an off-white solid. δH (DMSO-d6, 400 MHz): 0.93 (6H, d), 1.12 (3H, t), 1.57 (2H, m), 1.79 (2H, m), 2.03 (3H, m), 2.20 (1H, m), 2.81 (8H, m), 3.25 (2H, m), 7.32 (1H, t), 7.44 (2H, d), 7.67 (1H, d), 8.31 (1H, dd), 8.45 (1H, s), 12.06 (1H, br s). MS (ES): C29H34N4O2S requires 502. found 503.2 (M+H+).

Provenance & Evidence