Potassium Carbonate → HCID 25016592, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-chloro-4-fluoropyridine (904 mg, 6.87 mmol), 2-(2-aminoethyl)-6-(4-methylthiophen-2-yl)pyridazin-3(2H)-one (1470 mg, 6.25 mmol), and K2CO3 (1727 mg, 12.5 mmol) in DMF (8 mL) was stirred at 75° C. for 4 h. The mixture was partioned between CH2Cl2 (100 mL) and 5% NaHCO3 (50 mL). The organic layer was dried over MgSO4, concentrated, then purified on 40 g silica eluting with 20>60% of 2M NH3 in MeOH/CH2Cl2. Product isolated as a white solid. MS (ESI pos. ion) m/z (MH+): 347. Calc'd exact mass for C16H15ClN4OS: 346. 1H NMR (400 MHz, Chloroform-d) δ ppm 2.29 (s, 3 H) 3.61 (q, J=5.35 Hz, 2 H) 4.44-4.51 (m, 2 H) 5.31 (br. s., 1 H) 6.46 (s, 1 H) 6.94-7.01 (m, 2 H) 7.19 (s, 1 H) 7.57 (d, J=9.54 Hz, 1 H) 7.91 (d, J=6.02 Hz, 1 H). 13C NMR (101 MHz, Chloroform-d) δ ppm 15.76, 42.71, 50.46, 106.06, 107.27, 123.73, 128.21, 129.82, 130.08, 138.12, 138.76, 141.69, 149.32, 152.31, 155.06, 160.44.

Provenance & Evidence