Tetrahydrofuran → (4-{4-[6-(6-Trifluoromethyl-pyridin-3-ylamino)-pyridazin-3-yl]-phenyl}-cyclohexyl)-acetonitrile

Participants

Reaction Steps

To a mixture of 2-(4-{4-[6-(6-Trifluoromethyl-pyridin-3-ylamino)-pyridazin-3-yl]-phenyl}-cyclohexyl)-acetamide (0.18 g, 0.41 mmol, 1.0 equiv) in 3 Ml THF was added trifluoroacetic anhydride (0.068 Ml, 0.49 mmol, 1.2 equiv) followed by triethylamine (0.12 Ml, 0.90 mmol, 2.2 equiv). The reaction was stirred at ambient temperature overnight, and then concentrated in vacuo. Purification by silica gel chromatography (10-50% EtOAc in hexanes) afforded the title compound: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.39-1.50 (m, J=12.82, 12.54, 12.54, 3.54 Hz, 2H) 1.69-1.80 (m, J=12.88, 12.69, 12.69, 3.41 Hz, 2H) 1.86-1.97 (m, J=11.91, 11.91, 6.06, 5.87, 2.91 Hz, 1H) 2.09 (d, J=15.92 Hz, 1H) 2.09 (dd, J=5.94, 3.66 Hz, 3H) 2.76 (t, J=3.03 Hz, 1H) 7.53 (d, J=9.35 Hz, 1H) 7.59 (d, J=8.34 Hz, 2H) 8.08 (d, J=8.59 Hz, 1H) 8.20 (d, J=8.34 Hz, 2H) 8.30 (d, J=9.35 Hz, 1H) 8.91 (dd, J=8.59, 2.27 Hz, 1H) 9.16 (d, J=2.53 Hz, 1H) 10.25 (s, 1H); (M+H)+438.3.

Provenance & Evidence