Potassium Carbonate → HCID 71557022, compound

Participants

Reaction Steps

To a solution of 4-chloro-2-(pyrazolo[1,5-a]pyrimidin-3-yl)phenol (0.150 g, 0.61 mmol) and N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide (0.285 g, 0.64 mmol) in dimethylsulfoxide (5 mL) was added potassium carbonate (0.127 g, 0.92 mmol) and the mixture was stirred at ambient temperature for 4 h. The mixture was partitioned between ethyl acetate (100 mL) and water (20 mL). The organic phase was washed with brine (2×10 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue obtained was dissolved in dichloromethane (3 mL) and trifluoroacetic acid (3 mL). The reaction mixture was stirred for 3 h at ambient temperature and concentrated in vacuo. The residue was suspended in a mixture of dichloromethane and methanol (1:1, 50 mL) and filtered through a pad of diatomaceous earth. The filtrate was concentrated in vacuo and the residue that was triturated in ethyl acetate to afford 4-(4-chloro-2-(pyrazolo[1,5-a]pyrimidin-3-yl)phenoxy)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a beige solid in 68% yield (0.233 g): 1H NMR (300 MHz, DMSO-d6) δ9.20 (d, J=6.6 Hz, 1H), 8.77-8.70 (m, 1H), 8.61-8.45 (m, 3H), 7.82 (dd, J=9.1, 6.3 Hz, 1H), 7.38 (dd, J=8.3, 2.1 Hz, 1H), 7.28 (d, J=8.7 Hz, 1H), 7.23-7.09 (m, 2H); MS (ES+) m/z 520.7 (M+1), 522.7 (M+1).

Provenance & Evidence