Ammonia → 4-Carbamoyl-N-{2-[4-(4-fluorobenzoyl)piperidino]ethyl}-N-(2-methoxyphenyl)benzenesulfonamide

In an atmosphere of argon and with cooling in an ice bath, 4-{[N-[2-[4-(4-fluorobenzoyl)piperidino]ethyl}-2-methoxyanilino]-sulfonyl}benzoic acid (63 mg, 0.117 mmol) was dissolved in THF (1 ml) to which were subsequently added dropwise N-methylmorpholine (14 μl, 0.13 mmol) and isobutyl chloroformate (16.8 μl, 0.13 mmol). After 15 minutes of stirring at room temperature, 28% liquid ammonia (0.5 ml) was added to the reaction solution which was cooled in an ice bath, followed by additional 10 minutes of stirring at room temperature. The reaction mixture was extracted with methylene chloride, and the resulting organic layer was dried on anhydrous sodium carbonate. Thereafter, the solvent was removed by evaporation, and the resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1) to obtain 32 mg (50.9%) of the title compound in the form of light yellow oil.

1. temperatureIn an atmosphere of argon and with cooling in an ice bath
2. temperaturewas cooled in an ice bath
3. waitfollowed by additional 10 minutes
4. stirringof stirring at room temperature
5. extractionThe reaction mixture was extracted with methylene chloride
6. dry with materialthe resulting organic layer was dried on anhydrous sodium carbonate
7. customThereafter, the solvent was removed by evaporation
8. customthe resulting light yellow oily residue was purified by a silica gel column chromatography (ether-ethyl acetate-methylene chloride:methanol=10:1)

ORD record

ord-b00834c08920492095e2fbe7b5a3d02d

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05728835