Tetrahydrofuran → 4-(5-(4-chlorophenyl)-1,4-dimethyl-2-propionyl-1H-pyrrol-3-yl)benzene sulfonamide

Temperature

0 °C

Grignard reagent (ethyl magnesium bromide, 0.531 g, 3.98 ml, 1M soln. In THF, 3.98 mmol) was added dropwise under a nitrogen atmosphere to a stirred solution of 5-(4-chlorophenyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-N, 1,4-trimethyl-1H-pyrrole-2-carboxamide (compound 49ω, 0.400 g, 0.79 mmol) in anhydrous THF (15 ml) at 25° C., and the reaction mixture was then heated to about 70 to about 75° C. for 1 hr. The progress of the reaction was monitored by TLC. After cooling the reaction mixture to 0° C., the cooled reaction mixture was quenched by addition of saturated solution of ammonium chloride (10 ml). The mixture so formed was extracted with ethyl acetate (2×50 ml). The combined organic layer was dried over anhydrous Na2SO4. The solvent from the dried organic solution was evaporated under reduced pressure to obtain a crude product, which was then purified by preparative HPLC to obtain the title compound (0.070 g, 21.08%).

1. temperaturethe reaction mixture was then heated to about 70 to about 75° C. for 1 hr
2. customthe cooled reaction mixture
3. customwas quenched by addition of saturated solution of ammonium chloride (10 ml)
4. customThe mixture so formed
5. extractionwas extracted with ethyl acetate (2×50 ml)
6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
7. customThe solvent from the dried organic solution was evaporated under reduced pressure
8. customto obtain a crude product, which
9. customwas then purified by preparative HPLC

ORD record

ord-ca0168a4503047bda3ef3fd57754fdd6

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09393247B2