Cyclopentanone → HCID 66743778, compound

HRID 2363928Notes

Reaction equation

HRID 2363928 reaction equation
[CH3:1][NH:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[C:14]([NH2:16])=[O:15].O.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21](S(O)(=O)=O)=CC=1.C1(=O)CCCC1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:3]2[CH:7]=[C:6]([C:8]3[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=3)[S:5][C:4]=2[C:14](=[O:15])[NH:16][C:21]21[CH2:22][CH2:23][CH2:18][CH2:28]2

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 66743384HCID 66743384, compound

Product 1

HCID 66743778HCID 66743778, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(methylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (300 mg, 1.29 mmol), p-toluenesulfonic acid monohydrate (120 mg) and cyclopentan-1-one (10 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: DCM=1:9) to afford the title compound (200 mg, yield 52%) 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: DCM=1:9)

Sources & evidence

ORD record
ord-5cbd437c11a743eba80c18def47c37de
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

Loading…