Ammonium Hydroxide → HCID 178510373, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-{2-[3-(4-trifluoromethyl-1H-imidazol-2-yl)-1H-pyrazol-4-yl]-vinyl}-pyridine Compound 2 (50 mg, 0.164 mmole) and 5% aqueous ammonium hydroxide (20 mL) was stirred at 60° C. for 3 h until all of the starting material disappeared. After the solvent was removed in vacuo, the residue was dissolved in methanol and neutralized with several drops of 2M aqueous HCl to pH˜7. The solvent was evaporated and the crude compound was diluted with ethyl acetate and washed with water. The organic extracts were dried over MgSO4, filtered, and evaporated in vacuo. The product was purified by flash chromatography with 10% methanol/dichloromethane to give 2-[4-(2-pyridin-3-yl-vinyl)-1H-pyrazol-3-yl]-1H-imidazole-4-carbonitrile Compound 3 as a white solid (21.5 mg, 50%). 1H NMR (300 MHz, MeOD) δ 7.10 (d, J=16.5 Hz, 1H), 7.44 (dd, J=5, 7.8 Hz, 1H), 7.82 (d, J=14 Hz, 1H), 7.92 (s, 1H), 8.09 (d, J=7.7 Hz 1H), 8.18 (s, 1H), 8.37 (dd, J=1.5, 5 Hz, 1H), 8.63 (d, J=2 Hz, 1H); MS (ESI) m/z: 263.7 (M+H+).

Provenance & Evidence