P-Toluenesulfonylhydrazide → HCID 10459179, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3-chloro-phenyl)-3-[5-(3,4-dichloro-phenyl)-1-(4-ethoxy-phenyl)-1H-pyrazol-3-yl]-acrylic acid (Example 108, Step B; 0.043 g, 0.084 mmol) in EtOH (5 mL) was added tosylhydrazine (0.22 g, 1.2 mmol). To the light yellow solution was added a mixture of NaOAc (0.098 g, 1.2 mmol) in H2O (1 mL). The resulting mixture was heated to 100° C. overnight, then cooled to rt, diluted with H2O (10 mL), and extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried (MgSO4) and then concentrated to provide a yellow oil. The oil was purified by preparative reversed-phase HPLC (acetonitrile/water) to afford the pure alkane as a colorless oil (10 mg, 23%). TLC (silica gel, 9:1 CH2Cl2/MeOH): Rf=0.43. HPLC: Rt=10.7 (Method A). MS (ESI): mass calculated for C26H21Cl3N2O3, 514.06; m/z found, 513 [M−H]−. 1H NMR (400 mHz, CDCl3): 7.32-7.23 (m, 6H), 7.14-7.10 (m, 2H), 6.92-6.89 (m, 1H), 6.88-6.85 (m, 2H), 6.23 (s, 1H), 4.03 (q, J=6.9 Hz, 2H), 4.04-4.00 (m, 1H), 3.50 (dd, J=6.7, 14.7 Hz, 1H), 3.09 (dd, J=8.7, 14.7 Hz, 1H), (1.42 (t, J=7.0 Hz, 3H),

Provenance & Evidence