Pyridine → 5-(Acetylamino)methylimidazo[5,1-b]thiazole

HRID 1376596Notes

Reaction equation

HRID 1376596 reaction equation
[NH2:1][CH2:2][C:3]1[N:10]2[C:6]([S:7][CH:8]=[CH:9]2)=[CH:5][N:4]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12].N1C=CC=CC=1>C(Cl)Cl>[C:11]([NH:1][CH2:2][C:3]1[N:10]2[C:6]([S:7][CH:8]=[CH:9]2)=[CH:5][N:4]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 212623585-Aminomethylimidazo[5,1-b]thiazole

Product 1

HCID 229166995-(Acetylamino)methylimidazo[5,1-b]thiazoleYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 150 mg (0.98 mmol) of 5-aminomethylimidazo[5,1-b]thiazole in 1 ml of methylene chloride were added 1 ml of acetic anhydride and 0.5 ml of pyridine, and the mixture was stirred overnight at room temperature. The reaction solution was concentrated. The residue was dissolved in methylene chloride, and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography using silica gel, eluting with ethyl acetate to give 159 mg (yield 83%) of the title compound as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e108199616c24ebc956c7e61c3bed672
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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