Potassium Carbonate → HCID 46941040, 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), 2-chloro-N,N-dimethylacetamide (0.016 g, 0.13 mmol, 1.25 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 preparative HPLC (RP-C18, ACN/water) and trituration with Et2O gave the desired product. HPLC-MS: (5-100% B in 8 min, 0.8 mL/min): tR=4.68 min, [M+H]+ m/z 507.1; 1H NMR (300 MHz, CDCl3) δ 8.41 (d, J=1.7, 1H), 7.95 (d, J=1.8, 1H), 7.49 (s, 1H), 7.42 (d, J=2.1, 1H), 7.29 (d, J=2.1, 1H), 5.12-5.01 (m, 2H), 4.57 (d, J=9.2, 2H), 4.03-3.90 (m, 3H), 3.47 (s, 2H), 2.92 (s, 3H), 2.82 (s, 3H), 2.37 (d, J=0.6, 3H).

Provenance & Evidence