Cesium carbonate → HCID 85470480, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[(4-bromo-2-fluorophenyl)methyl]-7-phenyl-1λ6,2,7-thiadiazepane-1,1-dione (200 mg, 0.48 mmol), 1-(piperazin-1-yl)ethanone (93 mg, 0.72 mmol), Pd2(dba)3 (44 mg, 0.048 mmol), Xant-phos (55 mg, 0.096 mmol), and Cs2CO3 (469 mg, 1.44 mmol) in 1,4-dioxane (10 mL) under nitrogen atmosphere was stirred at 100° C. for 16 hours. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was purified by preparative HPLC to afford 2-{[4-(4-Acetylpiperazin-1-yl)-2-fluorophenyl]methyl}-7-phenyl-1λ6,2,7-thiadiaze-pane-1,1-dione as brown oil (68 mg, 31%). 1H NMR (500 MHz, CDCl3) δ ppm 7.35-7.40 (m, 6H), 6.67-6.69 (m, 1H), 6.55-6.58 (m, 1H), 4.50 (s, 2H), 3.76 (t, J=5.5, 2H), 3.60-3.65 (m, 4H), 3.36 (t, J=5.5, 2H), 3.16-3.21 (m, 4H), 2.14 (s, 3H), 1.98 (t, J=5, 2H), 1.90 (t, J=3.5, 2H); LCMS (ESI): m/z=234.9 [M-2-phenyl-1λ6,2,7-thiadiazepane-1,1-dione+H]+.

Provenance & Evidence