p-Toluenesulfonic acid → HCID 66743227, compound

HRID 2363938Notes

Reaction equation

HRID 2363938 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].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19](S(O)(=O)=O)=CC=1.C1(=O)CCCC1>C1(C)C=CC=CC=1>[N:13]1[CH:12]=[CH:11][C:10]([C:4]2[S:3][C:2]3[NH:1][C:19]4([CH2:20][CH2:21][CH2:16][CH2:26]4)[NH:9][C:7](=[O:8])[C:6]=3[CH:5]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8452CyclopentanoneHCID 66743788HCID 66743788, compound

Product 1

HCID 66743227HCID 66743227, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-amino-5-(pyridin-4-yl)thiophene-3-carboxamide (300 mg, 1.29 mmol), p-toluenesulfonic acid (150 mg) and cyclopentan-1-one (10 mL) in toluene (30 mL) was heated to reflux for 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 (90 mg), which was further purified by preparative TLC to give the title compound (55 mg, yield 15%) as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 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 (90 mg), which
  6. customwas further purified by preparative TLC

Sources & evidence

ORD record
ord-0e6ace3f24484cb9ba1cdaa64f82f582
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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