Hydrochloric Acid → HCID 59309618, compound

To a solution of 4-chloro-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-methoxybenzene-sulfonyl chloride (0.2 g) in methylene chloride (6 mL) were added 2-amino-2-phenylpropane (70 mg), triethylamine (0.11 mL) and 4-dimethylaminopyridine (6 mg), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in N,N-dimethylformamide (6 mL). To the solution were added methyl iodide (0.057 mL) and sodium hydride (55%, 22 mg) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in tetrahydrofuran (10 mL). To the solution was added hydrazine monohydrate (0.11 mL), and the mixture was heated at reflux for 2 hours. The reaction mixture was cooled to room temperature, and the insoluble material was removed by filtration. To the filtrate were added water and ethyl acetate, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1) to give the title compound (97 mg).

1. extractionthe resulting mixture was extracted with ethyl acetate
2. washThe extract was washed with water and brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customthe solvent was removed under reduced pressure
5. dissolutionThe residue was dissolved in N,N-dimethylformamide (6 mL)
6. additionTo the solution were added methyl iodide (0.057 mL) and sodium hydride (55%, 22 mg) under ice-
7. temperaturecooling
8. stirringthe mixture was stirred at room temperature for 1 hour
9. additionThe reaction mixture was poured into 1 mol/L hydrochloric acid
10. extractionthe resulting mixture was extracted with ethyl acetate
11. washThe extract was washed with water and brine
12. dry with materialdried over anhydrous magnesium sulfate
13. customThe solvent was removed under reduced pressure
14. dissolutionthe residue was dissolved in tetrahydrofuran (10 mL)
15. additionTo the solution was added hydrazine monohydrate (0.11 mL)
16. temperaturethe mixture was heated
17. temperatureat reflux for 2 hours
18. temperatureThe reaction mixture was cooled to room temperature
19. customthe insoluble material was removed by filtration
20. additionTo the filtrate were added water and ethyl acetate
21. customthe organic layer was separated
22. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
23. customthe solvent was removed under reduced pressure
24. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1)

ORD record

ord-091f3ad008414769ac63555357333ea0

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217069B2