Acetone → HCID 66744239, compound

HRID 2363939Notes

Reaction equation

HRID 2363939 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].O.[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1.CC(C)=O>C1(C)C=CC=CC=1>[CH3:18][C:17]1([CH3:22])[NH:1][C:2]2[S:3][C:4]([C:10]3[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=3)=[CH:5][C:6]=2[C:7](=[O:8])[NH:9]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 66743788HCID 66743788, compound

Product 1

HCID 66744239HCID 66744239, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-amino-5-(pyridin-4-yl)thiophene-3-carboxamide (300 mg, 1.37 mmol), p-toluenesulfonic acid monohydrate (150 mg) and acetone (30 mL) in toluene (30 mL) was heated to reflux overnight. After removal of the solvent, the residue was purified by column chromatography on silica gel (MeOH: dichloromethane=1:9) to afford the crude title compound (70 mg), which was further purified by preparative TLC to give the title compound (37 mg, yield 10%) as an orange solid:

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customAfter removal of the solvent
  4. customthe residue was purified by column chromatography on silica gel (MeOH: dichloromethane=1:9)
  5. customto afford the crude title compound (70 mg), which
  6. customwas further purified by preparative TLC

Sources & evidence

ORD record
ord-9e01762cf3334a439af703e5d9d9bc4f
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

Loading…