Sulfuric Acid → n-{5-(2-Methoxyethoxy)-2-[5-(morpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1h-indol-7-yl}-n,1-dimethyl-1h-imidazole-2-sulfonamide

온도

60 °C

To a mixture of N-[2-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-1H-indol-7-yl]-N,1-dimethyl-1H-imidazole-2-sulfonamide (580 mg), trifluoroacetic acid (7 mL) and water (14 mL) was added concentrated sulfuric acid (7 mL), and the mixture was stirred at 60° C. for 3 hr. The excess trifluoroacetic acid was evaporated under reduced pressure, and the residue was neutralized with sodium hydrogencarbonate. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The obtained crude product was dissolved in tetrahydrofuran (15 mL), morpholine (0.1 mL) was added, and the mixture was stirred at room temperature for 15 min. Sodium triacetoxyborohydride (466 mg) was added, and the mixture was stirred for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The residue was subjected to basic silica gel column chromatography (ethyl acetate:hexane=10:90-80:20) to give the title compound (183.5 mg, yield 30%) as a white solid.

1. customThe excess trifluoroacetic acid was evaporated under reduced pressure
2. extractionThe reaction mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltrated
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe obtained crude product
8. stirringthe mixture was stirred at room temperature for 15 min
9. stirringthe mixture was stirred for 1 hr
10. extractionthe mixture was extracted with ethyl acetate
11. washThe organic layer was washed with saturated brine
12. dry with materialdried over magnesium sulfate
13. filtrationfiltrated
14. concentrationthe filtrate was concentrated under reduced pressure

ORD 기록

ord-538ee580e44745379a59562f659fd177

출처 데이터셋

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07777047B2