Tetrahydrofuran → HCID 60169173, compound

Temperature

0 °C

Grignard reagent (Ethyl magnesium bromide, 0.42 g, 3.17 ml 1M solution in THF, 3.17 mmol) was added drop wise to a stirred solution of (5-(4-chlorophenyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)-3-methylphenyl)-N-methoxy-N,4-dimethylthiophene-2-carboxamide (41e, 0.33 g, 0.63 mmol) in anhydrous THF (20 ml) at 25° C. The reaction mixture was then heated to about 70° C. to 75° C. for 1 hr. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 0° C. The cooled reaction mixture was quenched by adding saturated solution of ammonium chloride (10 ml) and the mixture was then extracted with ethyl acetate (2×30 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, which was then purified by preparative HPLC to obtain the title compound (0.05 g, 18.1%)

1. temperatureThe reaction mixture was then heated to about 70° C. to 75° C. for 1 hr
2. customThe cooled reaction mixture
3. customwas quenched
4. additionby adding saturated solution of ammonium chloride (10 ml)
5. extractionthe mixture was then extracted with ethyl acetate (2×30 ml)
6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
7. customThe solvent was evaporated from the dried organic layer under reduced pressure
8. customto obtain a crude product, which
9. customwas then purified by preparative HPLC

ORD record

ord-f8f6ecdf94cb488e84f96e5f8da19d68

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09072731B2