Potassium Carbonate → HCID 86664207, 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 (0.030 g, 0.07 mmol, 1 eq) in dry DMF (0.8 mL), tert-butyl 2-bromoethylcarbamate (0.020 g, 0.09 mmol, 1.25 eq) and K2CO3 (0.01 g, 0.09 mmol, 1.25 eq) were added. The mixture was stirred at 105° C. for 2 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 preparative HPLC (RP-C18, ACN/water) gave the desired product (0.006 g, 15%). HPLC-MS: (50-100% B in 8 min, 0.8 mL/min): tR=1.75 min, [M+H]+ m/z 565; 1H NMR (300 MHz, CDCl3) δ/ppm 8.42 (d, J=1.7, 1H), 7.95 (d, J=1.8, 1H), 7.49 (s, 1H), 7.41 (t, J=2.5, 1H), 7.32 (t, J=4.5, 1H), 5.19 (s, 2H), 5.01 (s, 1H), 3.99 (s, 3H), 3.48-3.43 (m, 2H), 2.40-2.32 (m, 3H), 2.19-2.07 (m, 8H), 1.98 (s, 3H).

Provenance & Evidence