(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 58958573, compound

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Reaction Steps

To a solution of the crude N-[(1Z)-N-hydroxyethanimidoyl]-2-[(3-methyl-1-phenyl-1H-pyrazol-5-yl)amino]benzamide (257 mg, 0.41 mmol) in THF (3 mL) was added (methoxycarbonylsulfamoyl)triethylammonium hydroxide (Burgess reagent) (145 mg, 0.61 mmol). The flask was flushed with argon and refluxed for 3 h under argon. The reaction mixture was the cooled to rt, filtered through a small plug of silica gel, and the plug was eluted with EtOAc. The filtrate was concentrated under reduced pressure, and the residue purified by preparative TLC on silica gel using EtOAc/Hex (1:2, v/v) to give the title product as a solid (5.5 mg, 4% overall). 1H NMR (400 MHz, CD3CN). δ 2.30 (s, 3H), 2.32 (s, 3H), 3.82 (s, 3H), 6.16 (s, 1H), 7.09 (dd, 1H), 7.21 (d, 1H), 7.38-7.42 (m, 1H), 7.42-7.50 (m, 3H), 7.50-7.58 (m, 2H), 9.46 (br, s, 1H). ES-MS m/z 362.2 (MH+); HPLC RT (min) 3.28.

Provenance & Evidence