Pyridine → HCID 67280088, compound

Acetyl chloride (18 μL) was added dropwise to a mixture composed of di-tert-butyl {8-[(2,4-dimethoxybenzyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 42 (36 mg), pyridine (40 μL) and dehydrated dichloromethane (0.7 mL) under cooling in an ice bath. The ice bath was removed and the mixture was stirred for three hours. The reaction mixture was diluted with chloroform and then washed with a 0.2 N hydrochloric acid solution. The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and dichloromethane (1 mL) and 1,3-dimethoxybenzene (12 μL) were added to the resulting residue. Then, trifluoroacetic acid (1 mL) was added and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in chloroform and sequentially washed with a saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol) to obtain the title compound (15.6 mg, 76%) as a solid.

1. temperatureunder cooling in an ice bath
2. customThe ice bath was removed
3. additionThe reaction mixture was diluted with chloroform
4. washwashed with a 0.2 N hydrochloric acid solution
5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated under reduced pressure, and dichloromethane (1 mL) and 1,3-dimethoxybenzene (12 μL)
8. additionwere added to the resulting residue
9. additionThen, trifluoroacetic acid (1 mL) was added
10. stirringthe mixture was stirred at room temperature for 16 hours
11. concentrationThe reaction mixture was concentrated under reduced pressure
12. dissolutionThe resulting residue was dissolved in chloroform
13. washsequentially washed with a saturated sodium bicarbonate solution and brine
14. dry with materialThe organic layer was dried over anhydrous sodium sulfate
15. filtrationfiltered
16. concentrationThen, the filtrate was concentrated under reduced pressure
17. customThe resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol)

ORD record

ord-8f23d043108a448a8c9b54d3778b68fb

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158638B2