Hydrochloric Acid → HCID 23449031, compound

HRID 1839302Notes

Reaction equation

HRID 1839302 reaction equation
Cl.[N:2]([CH2:5][C:6]([C:8]1[N:9]=[CH:10][N:11]2[CH:15]=[CH:14][S:13][C:12]=12)=[O:7])=[N+]=[N-].[H][H].C1C[O:21][CH2:20][CH2:19]1>CO.[Pd]>[C:20]([NH:2][CH2:5][C:6]([C:8]1[N:9]=[CH:10][N:11]2[CH:15]=[CH:14][S:13][C:12]=12)=[O:7])(=[O:21])[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 23449280HCID 23449280, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23449031HCID 23449031, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution (17 ml) of 10% hydrochloric acid in methanol and 800 mg of 10%Pd—C. were added to a solution of 1.78 g of 7-azidoacetylimidazo[5,1-b]thiazole in 85 ml of methanol and 85 ml of THF. The atmosphere in the reactor was replaced with hydrogen. The system was stirred at room temperature for 5 hr. The catalyst was removed by filtration through Celite and washed with methanol. The solvent was removed by distillation. The residue was dissolved in 50 ml of DMF. Pyridine (3.43 ml) and 1.22 ml of acetic anhydride were added to the solution under ice cooling. The mixture was stirred at the same temperature for 2 hr. Dichloromethane and brine were added to the reaction solution. The mixture was adjusted to pH 10 by the addition of potassium carbonate. The organic layer were separated. The aqueous layer was further extracted five times with dichloromethane. The organic layers were combined together, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=40:1 to 20:1) to give 397 mg of 7-acetylaminoacetylimidazo[5,1-b]thiazole.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. washwashed with methanol
  3. customThe solvent was removed by distillation
  4. dissolutionThe residue was dissolved in 50 ml of DMF
  5. additionPyridine (3.43 ml) and 1.22 ml of acetic anhydride were added to the solution under ice cooling
  6. stirringThe mixture was stirred at the same temperature for 2 hr
  7. additionDichloromethane and brine were added to the reaction solution
  8. additionThe mixture was adjusted to pH 10 by the addition of potassium carbonate
  9. customThe organic layer were separated
  10. extractionThe aqueous layer was further extracted five times with dichloromethane
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated under the reduced pressure
  14. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=40:1 to 20:1)

Sources & evidence

ORD record
ord-7147f4211b504659bdb93c950144eb6c
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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