Trifluoroacetic acid → 2-amino-N-(4-p-tolylthiazol-2-yl)thiazole-5-carboxamide

HRID 1188137Notes

Reaction equation

HRID 1188137 reaction equation
C(O)(C(F)(F)F)=O.[C:8]1([CH3:35])[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([NH:19][C:20]([C:22]3[S:26][C:25]([NH:27]C(=O)OC(C)(C)C)=[N:24][CH:23]=3)=[O:21])[S:17][CH:18]=2)=[CH:10][CH:9]=1>C(Cl)(Cl)Cl>[NH2:27][C:25]1[S:26][C:22]([C:20]([NH:19][C:16]2[S:17][CH:18]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([CH3:35])=[CH:9][CH:10]=3)[N:15]=2)=[O:21])=[CH:23][N:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86643475Tert-butyl 5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-ylcarbamate

Product 1

HCID 594087592-amino-N-(4-p-tolylthiazol-2-yl)thiazole-5-carboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

TFA (0.100 mL) was added to a solution of tert-butyl 5-(4-p-tolylthiazol-2-ylcarbamoyl)thiazol-2-ylcarbamate (80 mg, 0.19 mmol) in CHCl3 (1 mL). The resulting solution was stirred at RT overnight. Then the solvents were evaporated and the crude product was dissolved in H2O. After neutralization with NaHCO3 saturated aqueous solution, it was extracted with AcOEt, dried and concentrated. Purification by column chromatography (100% AcOEt) yielded 2-amino-N-(4-p-tolylthiazol-2-yl)thiazole-5-carboxamide (40 mg, 67%) as a white solid.

Workup

  1. customThen the solvents were evaporated
  2. dissolutionthe crude product was dissolved in H2O
  3. extractionAfter neutralization with NaHCO3 saturated aqueous solution, it was extracted with AcOEt
  4. customdried
  5. concentrationconcentrated
  6. customPurification by column chromatography (100% AcOEt)

Sources & evidence

ORD record
ord-25607bf9fc20440aa32123cae8a9dd31
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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