1-benzofuran-3-sulfonamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The above prepared benzofuran-3-sulfonic acid amide (0.050 g, 0.254 mmol) was dissolved in 1.5 mL of abs. acetonitrile and treated successively with triethylamine (0.088 mL, 2.5 eq.) and phenyl chloroformate (0.0397 g, 1.0 eq.), and the mixture was then kept at ambient temperature for 1 h. 1-(6-Amino-4-methylsulfanyl-pyridin-2-yl)-3-methyl-urea (see below, 0.0538 g, 1.0 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, MeOH/AcOEt=5/95) and crystallization from AcOEt/heptane, delivered eventually 0.016 g of the title compound as off-white solid. was dissolved in 1.5 mL of abs was then added Cooling pouring ice, twofold extraction with AcOEt washing with water drying over sodium sulfate, and evaporation of the solvents followed by flash chromatography (SiO2, MeOH/AcOEt=5/95) and crystallization from AcOEt/heptane

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To the above prepared benzofuran-3-sulfonyl chloride (0.104 g, 0.480 mmol) was added ammonia (6 eq., 0.5 M in dioxane) and the mixture stirred for one night at 50° C. Evaporation of the solvent, followed by flash chromatography (SiO2, heptane/AcOEt=7/3) and direct crystallization from heptane/AcOEt, generated 0.036 g of the title compound as off-white crystals. Extensive nOE measurements and 13C-NMR NMR corroborated the structure. Evaporation of the solvent followed by flash chromatography (SiO2, heptane/AcOEt=7/3) and direct crystallization from heptane/AcOEt

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The below prepared benzofuran-3-sulfonic acid amide (0.051 g, 0.259 mmol) was dissolved in 1.5 mL of abs. acetonitrile and treated successively with triethylamine (0.090 mL, 2.5 eq.) and phenyl chloroformate (0.0405 g, 1.0 eq.), and the mixture was then kept at ambient temperature for 1 h. 4-Bromo-pyridine-2,6-diamine (0.0486 g, 1.0 eq.), dissolved in a tiny amount of acetonitrile, was added, and the mixture heated to 60° C. for 18 h. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=3/7) and crystallization from AcOEt/heptane, yielded finally 0.015 g of the title compound as off-white solid. was dissolved in 1.5 mL of abs was added Cooling pouring ice, twofold extraction with AcOEt washing with water drying over sodium sulfate, and evaporation of the solvents followed by flash chromatography (SiO2, hexane/AcOEt=3/7) and crystallization from AcOEt/heptane