Tetrahydrofuran → HCID 71187164, compound

Participants

Reaction Conditions

Reaction Steps

Grignard reagent (ethyl magnesium bromide, 1.32 g, 9.9 ml, 9.97 mmol) was added drop wise to a stirred solution of 5-(4′-(N-((dimethylamino)methylene)sulfamoyl)-6-methoxy-[1,1′-biphenyl]-3-yl)-N-methoxy-N,4-dimethylthiophene-2-carboxamide (1d, 1.0 g, 1.99 mmol) in anhydrous THF (20 ml) at 25° C. The reaction mixture was heated at 80-85° C. for 1 hour. The progress of the reaction was monitored by TLC. The reaction mixture was cooled to 0° C. The cooled reaction mixture was then quenched by adding a saturated solution of ammonium chloride (10 ml). The mixture was then extracted with ethyl acetate (3×60 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent was evaporated from the dried organic layer under reduced pressure to obtain a crude product. The crude product so obtained was purified by flash chromatography using 30-40% ethyl acetate in hexane as an eluent to obtain the title compound. The compound was re-purified by dissolving 0.68 g of the compound in ethyl acetate (5 ml) and precipitating it by slow addition of diisopropyl ether. (0.180 g, 21.7%).

Provenance & Evidence