2-Carbamimidoylsulfanyl-3-oxo-3-(2-trifluoromethyl-phenyl)-propionamide → 2-Amino-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

HRID 1667655Notes

Reaction equation

HRID 1667655 reaction equation
[C:1]([S:4][CH:5]([C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([F:19])([F:18])[F:17])[C:6]([NH2:8])=[O:7])(=[NH:3])[NH2:2]>C(O)C>[NH2:2][C:1]1[S:4][C:5]([C:6]([NH2:8])=[O:7])=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:3]=1

Participants

3

Reactant 1

HCID 866427932-Carbamimidoylsulfanyl-3-oxo-3-(2-trifluoromethyl-phenyl)-propionamide

Product 1

HCID 593753502-Amino-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amideYield 69.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.00 g (0.0066 mole) of 2-carbamimidoylsulfanyl-3-oxo-3-(2-trifluoromethyl-phenyl)-propionamide in 80 mL of ethanol was heated to 60 degrees for overnight. The mixture was concentrated under reduce pressure. Purification of the residue by chromatography on C18-reverse phase silica gel, eluting with water-acetonitrile (gradient 100:0-50:50) gave 1.32 g of 2-amino-4-(2-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (V.17) as a yellow solid.

Workup

  1. temperaturewas heated to 60 degrees for overnight
  2. concentrationThe mixture was concentrated
  3. customPurification of the residue by chromatography on C18-reverse phase silica gel
  4. washeluting with water-acetonitrile (gradient 100:0-50:50)

Sources & evidence

ORD record
ord-af204ebd9d2a4c2ab42abeb9a2e1464a
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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