Potassium Carbonate → HCID 58204683, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-piperidin-4-yl-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene trifluoro acetate (300 mg, 0.61 mmol) in DMF (3.5 mL) was added potassium carbonate (290 mg, 2.1 mmol) and 2-(2-bromoethoxy)tetrahydro-2H-pyran and the mixture heated at 60° C. for 18 h before being diluted with DCM. The resultant solution was washed with saturated aqueous sodium hydrogen carbonate, water and then brine before being dried (MgSO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 8% methanol in DCM) to give 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-8-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-piperidin-4-yl}-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene as a cream solid (147 mg, 48%). 1H NMR 400 MHz (CDCl3) δ: 8.44 (1H, d, J=8.29 Hz), 7.87 (1H, s), 7.63 (1H, s), 7.04 (1H, dd, J=8.33, 1.81 Hz), 6.92 (1H, d, J=1.75 Hz), 6.01-6.00 (1H, m), 4.63 (1H, t, J=3.54 Hz), 4.46-4.45 (4H, m), 3.92-3.91 (2H, m), 3.65 (1H, m), 3.57-3.49 (1H, m), 3.15 (2H, m), 2.73 (2H, m), 2.53 (1H, m), 2.25 (2H, m), 1.87 (5H, m), 1.73-1.69 (3H, m), 1.60 (8H, m).

Provenance & Evidence