Sodium Acetate → HCID 11443036, compound

Participants

Reaction Steps

A stirred solution of (E)-3-[4-(3,4-dichloro-phenyl)-5-(4-methoxy-phenyl)-1H-imidazol-2-yl]-2-m-tolyl-acrylic acid (Example 17; 50 mg, 0.084 mmol), p-toluenesulfonylhydrazide (0.24 g, 1.26 mmol) and NaOAc (0.10 g, 1.26 mmol) in EtOH (1.0 mL) was heated to 85° C. for 16 h. The reaction mixture was cooled and then purified directly by reversed-chromatography (Method B) to afford the title compound (10 mg, 20%). HPLC: Rt=1.19 (Method D). MS (ESI): mass calculated for C26H22Cl2N2O3, 480.10; m/z found, 481.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.54 (d, J=2.0 Hz, 1H), 7.44 (d, J=8.3 Hz, 1H), 7.34-7.29 (m, 2H), 7.27 (dd, J=8.3, 2.0 Hz, 1H), 7.23 (d, J=7.6 Hz, 1H), 7.17-7.10 (m, 3H), 6.96-6.91 (m, 2H), 4.40 (dd, J=10.1, 5.8 Hz, 1H), 3.86 (s, 3H), 3.61 (dd, J=14.9, 10.1 Hz, 1H), 3.29 (dd, J=14.9, 5.8 Hz, 1H), 2.34 (s, 3H).

Provenance & Evidence