Triethylamine → HCID 67280520, compound

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 (47 mg), triethylamine (36 μl), dichloromethane (1 ml) and 4-chlorobutyryl chloride (14 μl) was stirred at room temperature for 12 hours. A 0.1 N sodium hydroxide solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in dehydrated dichloromethane (1.5 ml). 1,3-Dimethoxybenzene (16 μl) and trifluoroacetic acid (1.5 ml) was added and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and a 0.1 N sodium hydroxide solution was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. Dimethylformamide (1 ml) and potassium tert-butoxide (15 mg) were added to the resulting residue, and the mixture was stirred at room temperature for two hours. The reaction mixture was separated with water and chloroform. Then, the organic layer was dried over sodium sulfate and filtered, and 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 (13 mg, 46%) as a solid.

1. extractionfollowed by extraction with ethyl acetate
2. dry with materialThe organic layer was dried over sodium sulfate
3. filtrationfiltered
4. concentrationThen, the filtrate was concentrated under reduced pressure
5. dissolutionThe resulting residue was dissolved in dehydrated dichloromethane (1.5 ml)
6. addition1,3-Dimethoxybenzene (16 μl) and trifluoroacetic acid (1.5 ml) was added
7. stirringthe mixture was stirred at room temperature overnight
8. concentrationThe reaction mixture was concentrated under reduced pressure
9. additiona 0.1 N sodium hydroxide solution was added to the resulting residue
10. extractionfollowed by extraction with ethyl acetate
11. dry with materialThe organic layer was dried over sodium sulfate
12. filtrationfiltered
13. concentrationThen, the filtrate was concentrated under reduced pressure
14. additionDimethylformamide (1 ml) and potassium tert-butoxide (15 mg) were added to the resulting residue
15. stirringthe mixture was stirred at room temperature for two hours
16. customThe reaction mixture was separated with water and chloroform
17. dry with materialThen, the organic layer was dried over sodium sulfate
18. filtrationfiltered
19. concentrationthe filtrate was concentrated under reduced pressure
20. customThe resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol)

ORD record

ord-416df920bb9147759b03a1242b3d0a27

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158638B2