Triethylamine → N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide

Under a nitrogen atmosphere, a solution of N-[2-(3-amino-7-benzyloxyquinolin-4-ylamino)-1,1-dimethylethyl]methanesulfonamide (12.6 g, 30.4 mmol) in dichloromethane (300 mL) was cooled to approximately 0° C.; triethylamine (4.23 mL, 30.4 mmol) was added. Ethoxy acetyl chloride (3.33 mL, 30.4 mmol) was added dropwise, and the reaction was stirred at ambient temperature for 1.5 hours. The volatiles were removed under reduced pressure, and the residue was dissolved in ethanol (300 mL). Triethylamine (13 mL) was added, and the reaction was heated at reflux overnight and allowed to cool to ambient temperature. The volatiles were removed under reduced pressure. The residue was dissolved in dichloromethane (300 mL), and the resulting solution was washed with water (2×100 mL) and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide a brown oil. The oil was purified by column chromatography on silica gel (eluting with 97.5:2.5 chloroform:methanol) to provide 12.4 g of N-[2-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as a beige solid.

1. customThe volatiles were removed under reduced pressure
2. dissolutionthe residue was dissolved in ethanol (300 mL)
3. additionTriethylamine (13 mL) was added
4. temperaturethe reaction was heated
5. temperatureat reflux overnight
6. temperatureto cool to ambient temperature
7. customThe volatiles were removed under reduced pressure
8. dissolutionThe residue was dissolved in dichloromethane (300 mL)
9. washthe resulting solution was washed with water (2×100 mL) and brine
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customto provide a brown oil
14. customThe oil was purified by column chromatography on silica gel (eluting with 97.5:2.5 chloroform:methanol)

ORD 기록

ord-8f019e9bf5244edf9d63d14aa577ec2a

출처 데이터셋

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07923560B2