Potassium Carbonate → HCID 66717245, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(5-(6-amino-5-(trifluoromethyl)pyridin-3-yl) -6-methylimidazo[2,1-b][1,3,4]thiadiazol-2-yl)-2-methoxyphenol (0.042 g, 0.1 mmol, 1 eq) in dry DMF (1 mL), 4-(2-chloroethyl)morpholine hydrochloride (0.024 g, 0.13 mmol, 1.25 eq), iPr2EtN (0.021 mL, 0.13 mmol, 1.3 eq) and K2CO3 (0.018 g, 0.13 mmol, 1.25 eq) were added. The mixture was stirred at 105° C. for 1 h and cooled to RT. The solvent was evaporated, and the dry residue was taken up in DCM, washed with water (2×1 mL), dried (MgSO4), filtered and concentrated to dryness. Purification by reversed-phase chromatography (RP-C18, ACN/water) using a pre-packed cartridge and, subsequently, preparative HPLC gave the desired product. HPLC-MS: (5-100% B in 8 min, 0.6 mL/min): tR=3.3 min, [M+H]+ m/z 534.1; 1H NMR (300 MHz, CDCl3) δ/ppm 8.44 (d, J=1.7, 1H), 7.98 (d, J=1.8, 1H), 7.49 (d, J=0.8, 1H), 7.41 (d, J=2.0, 1H), 7.31 (d, J=2.1, 1H), 5.07 (s, 2H), 4.01-3.89 (m, 6H), 3.69-3.59 (m, 4H), 3.47 (s, 3H), 2.62-2.51 (m, 3H), 2.38 (dd, J=9.0, 2.7, 7H).

Provenance & Evidence