Potassium Carbonate → 2-(3,4-dichlorophenyl)-5-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridazin-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 1-(3,4-dichlorophenyl)-6-oxo-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)-1,6-dihydropyridazine-3-carboxylic acid (15 mg, 0.03 mmol) in NMP (2 mL) at room temperature under argon was added K2CO3 (8.22 mg, 0.06 mmol). The reaction mixture was heated at 150° C. overnight. The crude product was directly purified by preparative HPLC (C18 column; 10-100% methanol in water without TFA) to give 2-(3,4-dichlorophenyl)-5-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridazin-3(2H)-one (9.5 mg, tan solid, 66%). 1H NMR (400 MHz, CDCl3) δ ppm 0.93 (t, J=7.47 Hz, 2H) 1.38-1.72 (m, 2H) 1.81-2.02 (m, 2H) 2.00-2.21 (m, 2H) 2.40 (t, J=7.69 Hz, 2H) 3.50-3.80 (m, 2H) 4.06-4.37 (m, 2H) 4.47-4.68 (m, 1H) 5.56 (s, 1H) 7.28 (dd, J=8.57, 2.42 Hz, 2H) 7.44-7.72 (m, 2H) 8.16 (s, 2H). MS (ESI) 461 (M+H).

Provenance & Evidence