N-{5-[(tert-Butylamino)sulfonyl]-4-methyl-1,3-thiazol-2-yl)acetamide → N-(4-methyl-5-sulfamoylthiazol-2-yl)acetamide

HRID 1024929Notes

Reaction equation

HRID 1024929 reaction equation
C([NH:5][S:6]([C:9]1[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=1[CH3:18])(=[O:8])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:5][S:6]([C:9]1[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][C:10]=1[CH3:18])(=[O:7])=[O:8]

Participants

3

Reactant 1

HCID 59257550N-{5-[(tert-Butylamino)sulfonyl]-4-methyl-1,3-thiazol-2-yl)acetamide

Product 1

HCID 3244062N-(4-methyl-5-sulfamoylthiazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-{5-[(tert-butylamino)sulfonyl]-4-methyl-1,3-thiazol-2-yl}acetamide (1.1 g) in TFA (10 ml) was stirred at room temperature for 3d. The mixture was evaporated, redissolved in TFA (10 ml) and stirred for a further 1 d. On evaporation the resulting oil was azeotroped with DCM (×2) and triturated with Et2O to give the subtitle compound as a beige solid. Yield 0.7 g.

Workup

  1. customThe mixture was evaporated
  2. dissolutionredissolved in TFA (10 ml)
  3. customOn evaporation the resulting oil
  4. customwas azeotroped with DCM (×2)
  5. customtriturated with Et2O

Sources & evidence

ORD record
ord-eb7b1297e7b54f8bbe309ca159bef44d
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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