2-[Bis(methylthio)methylene]-4-butyl-4-methylnaphthalene-1,3(2h,4h)-dione → Tert-butyl 3-(4-butyl-1-hydroxy-4-methyl-3-oxo-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4h-1,2,4-benzothiadiazin-7-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

A solution of Example 27F (0.296 g, 0.885 mmol) and (4-amino-3-sulfamoyl-phenyl)-carbamic acid tert-butyl ester (0.280 g, 0.973 mmol) in toluene (40 mL) was refluxed for 6 hours. The solution was cooled to 25° C. and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane followed by 20% and 30% ethyl acetate in hexane to give the title compound (0.430 g, 92%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.53 (m, 1 H) 0.69 (m, 3 H) 0.87 (m, 1 H) 1.08 (m, 2 H) 1.46 (m, 9 H) 1.55 (m, 3 H) 2.01 (m, 1 H) 2.20 (m, 1 H) 7.60 (m, 5 H) 8.13 (m, 2 H) 9.83 (m, 1 H) 13.93 (m, 1 H). MS (ESI−) m/z 524 (M−H)−.

Provenance & Evidence