Cesium carbonate → 2-[[3-(4,4-dibutyl-1-hydroxy-3-oxo-2-naphthyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]oxy]acetamide

Participants

Reaction Steps

A solution of the product of Example 5E (69 mg, 0.15 mmol), 2-bromoacetamide (80 mg, 0.58 mmol), cesium carbonate (96 mg, 0.58 mmol), and tetrabutylammonium iodide (26 mg, 0.08 mmol) in N,N-dimethylformamide (2.4 mL) was stirred at 25° C. for 48 hours, diluted with ethyl acetate and treated with saturated ammonium chloride solution (2 mL). The organic layer was washed with water (3×) and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (58 mg, 76%). 1H NMR (300 MHz, DMSO-d6): δ 13.73 (s, 1 H), 8.17 (d, J=7.72 Hz, 1 H), 7.74 (m, 3 H), 7.55 (m, 1 H), 7.40 (m, 2 H), 4.59 (s, 2 H), 2.19 (m, 2 H), 2.02 (d, 2 H), 1-06 (m, 4 H), 0.90 (m, 2H), 0.69 (q, J=7.60 Hz, 6 H), 0.52 (m, 2 H).

Provenance & Evidence