Imidazole → 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-4-(1H-imidazol-1-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 2-{[3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}-4-fluorobenzoate (Example 246, 50 mg, 0.13 mmol), imidazole (17.8 mg, 0.26 mmol), and potassium carbonate (90.6 mg, 0.66 mmol) was added DMF (1 mL). The mixture was then heated to 110° C. for 16 h. The reaction mixture was allowed to cool to rt. The solvent was removed under reduced pressure, and the crude was purified by HPLC purification using gradient elution from 10 to 80% acetonitrile in water to afford 13.8 mg (25%) of the title compound. 1H NMR (300 MHz, CD3OD) δ 9.48 (t, 1H), 8.15 (d, 1H), 8.07 (t, 1H), 7.76 (t, 1H), 7.52 (d, 1H), 7.28-7.42 (m, 4H), 7.10 (dd, 1H), 6.48 (s, 1H), 2.06 (s, 3H), 1.35 (s, 9H). ES-MS m/z 416.2 (MH+); HPLC RT (min) 2.21.

Provenance & Evidence