Cyclopentanone → HCID 66743184, compound

HRID 2364040Notes

Reaction equation

HRID 2364040 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:9])=[O:8])=[C:4]([NH:10][CH2:11][CH3:12])[CH:3]=1.[C:13]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14]1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[Br:1][C:2]1[S:6][C:5]2[C:7](=[O:8])[NH:9][C:13]3([CH2:17][CH2:16][CH2:15][CH2:14]3)[N:10]([CH2:11][CH3:12])[C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 8452CyclopentanoneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 66743701HCID 66743701, compound

Product 1

HCID 66743184HCID 66743184, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-3-(ethylamino)thiophene-2-carboxamide (500 mg, 2.0 mmol), cyclopentanone (0.53 mL, 6.0 mmol), CSA (46 mg, 0.20 mmol), MgSO4 (384 mg, 4.0 mmol) and DMA (1.5 mL) was stirred at 90° C. for 1 day. The mixture was poured into saturated aqueous NaHCO3. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to 50:50 hexane/EtOAc) to give a brown solid. The solid was washed with EtOAc to give the title compound (352 mg, 56%) as a pale brown solid:

Workup

  1. extractionThe organic materials were extracted with EtOAc
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customAfter removal of the solvent at reduced pressure
  6. customthe residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to 50:50 hexane/EtOAc)
  7. customto give a brown solid
  8. washThe solid was washed with EtOAc

Sources & evidence

ORD record
ord-c5a90e1123274a33af7521819fb29104
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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