Hydrochloric Acid → n-2-(2-Thien-3-yl-5-pyridyl)propyl 2-propanesulfonamide

To an ambient temperature solution of 214 mg,(l mmol) of material prepared in step A in 5 ml of THF was added dropwise 0.11 ml of a 10 M solution borane-methyl sulfide complex (1.1 mmol) in THF. The mixture was stirred at ambient temperature for 2 h. Then, 0.1 ml of a 10 M solution borane-methyl sulfide complex (1.0 mmol) in THF were added and the mixture stirred overnight. A saturated solution of hydrochloric acid in methanol (5 ml) was added, and stirred for 10 min. The solution was concentrated in vacuo. The crude was disolved in dichloromethane (5 ml) and cooled to 0° C., triethylamine 0.44 ml (3.2 mmol) was added, followed by isopropylsulfonyl chloride (0.14 ml, 1.2 mmol). The ice-bath was removed and the solution was stirred at ambient temperature for 2 h. The organic solution was washed with 1N hydrochloric acid, sodium bicarbonate saturated solution, brine, dried over Na2SO4 filtered and concentrated in vacuo. Chromatography (50 g of silica gel, 33% ethyl acetate/hexane) of the residue afforded 25 mg (7%) of the title compound. Field Desorption Mass Spectrum: M=324.

1. stirringthe mixture stirred overnight
2. stirringstirred for 10 min
3. concentrationThe solution was concentrated in vacuo
4. temperaturecooled to 0° C.
5. customThe ice-bath was removed
6. stirringthe solution was stirred at ambient temperature for 2 h
7. washThe organic solution was washed with 1N hydrochloric acid, sodium bicarbonate saturated solution, brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-75279ff8871a40b0a14bbe0bf71aacc6

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06596716B2