Triethylamine → 7-(t-Butyldimethylsilylsulfamoyl)imidazo[5,1-b]thiazole

HRID 1839313Notes

Reaction equation

HRID 1839313 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:16]([C:20]1[N:21]=[CH:22][N:23]2[CH:27]=[CH:26][S:25][C:24]=12)(=[O:19])(=[O:18])[NH2:17].C(OCC)(=O)C>CN(C=O)C>[Si:1]([NH:17][S:16]([C:20]1[N:21]=[CH:22][N:23]2[CH:27]=[CH:26][S:25][C:24]=12)(=[O:19])=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 234491397-Sulfamoylimidazo[5,1-b]thiazole

Product 1

HCID 178110667-(t-Butyldimethylsilylsulfamoyl)imidazo[5,1-b]thiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butyldimethylsilyl chloride (0.30 g) and 0.33 ml of triethylamine were added to a solution of 0.20 g of 7-sulfamoylimidazo[5,1-b]thiazole in 5 ml of DMF. The mixture was stirred at room temperature for one hr. Ethyl acetate was added to the reaction mixture, followed by washing with water and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 0.34 of 7-(t-butyldimethylsilylsulfamoyl)imidazo[5,1-b]thiazole.

Workup

  1. washby washing with water and saturated brine in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b8f13980e84544b0ba42ca0e5a31f8b8
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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