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

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Example 2G (14 mg, 0.032 mmol), 2-bromoacetamide (9 mg, 0.064 mmol), cesium carbonate (22 mg, 0.067 mmol) and tetrabutylammonium iodide (3 mg) in N,N-dimethylformamide (0.5 mL) was stirred at 25° C. for 18 hours. The solution was acidified with 1M citric acid solution (1 mL) and extracted with ethyl acetate. The organic layer was washed with water (3×) and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo. A suspension of the residue in acetonitrile (2 mL) was treated with 1N sodium hydroxide solution (26 μL) and stirred at 25° C. for 2 hours. The solution was lyophilized to afford the title compound (12 mg, 52%). 1H NMR (300 MHz, DMSO-d6): δ 8.12 (d, J=8.09 Hz, 1 H), 7.61 (m, 4 H), 7.31 (m, 2 H), 4.55 (s, 2 H), 2.15 (m, 2H), 1.87 (m, 2 H), 1.29 (m, 2 H), 0.87 (m, 2 H), 0.60 (m, 7 H).

Provenance & Evidence