tert-butyl N-{4-methyl-5-[(2,4,6-trimethylphenyl)carbamoyl]-1,3-thiazol-2-yl}carbamate → 5-Thiazolecarboxamide, 2-amino-4-methyl-N-(2,4,6-trimethylphenyl)-

HRID 9089Notes

Reaction equation

HRID 9089 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11]([C:13]1[S:17][C:16]([NH:18]C(=O)OC(C)(C)C)=[N:15][C:14]=1[CH3:26])=[O:12]>FC(F)(F)C(O)=O>[NH2:18][C:16]1[S:17][C:13]([C:11]([NH:10][C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[O:12])=[C:14]([CH3:26])[N:15]=1

Participants

3

Reactant 1

HCID 9820995tert-butyl N-{4-methyl-5-[(2,4,6-trimethylphenyl)carbamoyl]-1,3-thiazol-2-yl}carbamate

Product 1

HCID 2108135-Thiazolecarboxamide, 2-amino-4-methyl-N-(2,4,6-trimethylphenyl)-Yield 91.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [5-[[(2,4,6-Trimethylphenyl)amino]carbonyl]-4-methyl-2-thiazolyl]carbamic acid, 1,1-dimethylethyl ester (10 g, 26.63 mmol) in trifluoroacetic acid (100 mL) was stirred at rt for 3 h. The solution was concentrated under reduced pressure and the residue was diluted with EtOAc (700 mL), washed with 5% aq. KHCO3 solution (400 mL, 2×), water, and brine; dried (MgSO4), filtered and concentrated. The residue was washed with ether (200 mL) and acetonitrile (100 mL) to obtain the title compound (6.7 g, 91%) as a white solid.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionthe residue was diluted with EtOAc (700 mL)
  3. washwashed with 5% aq. KHCO3 solution (400 mL, 2×), water, and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe residue was washed with ether (200 mL) and acetonitrile (100 mL)

Sources & evidence

ORD record
ord-95939283827b413aa59601d91194e5dd
Source dataset
uspto-grants-2006_08
Patent number
US07091223B2

Reaction notes

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