Chlorotrimethylsilane → HCID 23449267, compound

7-Acetylimidazo[5,1-b]thiazole (2.49 g) was dissolved in a solution of 150 ml of THF and 30 ml of HMPA. A 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (18 ml) was added dropwise to the solution in an argon atmosphere at −70° C. The mixture was stirred at the same temperature for 30 min. Trimethylsilyl chloride (2.28 ml) was added dropwise thereto. The mixture was stirred at the same temperature for 30 min. A solution of 3.21 g of N-bromosuccinimide in 90 ml of THF was added dropwise thereto. The mixture was stirred for 2 hr while raising the temperature to room temperature. Ethyl acetate (400 ml) was added to the reaction solution. The mixture was washed twice with brine, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation under the reduced pressure. The residue was dissolved in 120 ml of DMF. Sodium acetate (1.48 g) was added to the solution. The mixture was stirred at room temperature for 14 hr and then at 60° C. for 4 hr. The reaction solution was concentrated under the reduced pressure until the amount of the solution became half. Brine (290 ml) was added to the concentrate, followed by extraction twice with 300 ml of ethyl acetate. The organic layers were combined together, washed three times with brine, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (eluting with dichloromethane:ethyl acetate=1:1 and then with ethyl acetate) to give 2.11 g of 7-acetoxyacetylimidazo[5,1-b]thiazole.

1. stirringThe mixture was stirred at the same temperature for 30 min
2. stirringThe mixture was stirred for 2 hr
3. washThe mixture was washed twice with brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customThe solvent was removed by distillation under the reduced pressure
7. dissolutionThe residue was dissolved in 120 ml of DMF
8. additionSodium acetate (1.48 g) was added to the solution
9. stirringThe mixture was stirred at room temperature for 14 hr
10. waitat 60° C. for 4 hr
11. concentrationThe reaction solution was concentrated under the reduced pressure until the amount of the solution
12. additionBrine (290 ml) was added to the concentrate
13. extractionfollowed by extraction twice with 300 ml of ethyl acetate
14. washwashed three times with brine
15. dry with materialdried over anhydrous magnesium sulfate
16. filtrationfiltered
17. customThe solvent was removed by distillation under the reduced pressure
18. customThe residue was purified by column chromatography on silica gel (
19. washeluting with dichloromethane

ORD record

ord-c73d4bce37894cdfae22ddb5c36f32c6

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06677331B2