Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 66743871, compound

HRID 2364032Notes

Reaction equation

HRID 2364032 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:9])=[O:8])=[C:4]([NH:10][CH3:11])[CH:3]=1.[F:12][C:13]([F:19])([F:18])[CH2:14][C:15](=O)[CH3:16].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:15]([CH3:16])([CH2:14][C:13]([F:19])([F:18])[F:12])[N:10]([CH3:11])[C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 5390014,4,4-Trifluorobutan-2-oneHCID 66743363HCID 66743363, compound

Product 1

HCID 66743871HCID 66743871, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 5-bromo-3-(methylamino)thiophene-2-carboxamide (940 mg, 4.0 mmol), 4,4,4-trifluorobutan-2-one (5.04 g, 40 mmol), CSA (93 mg, 0.40 mmol), MgSO4 (576 mg, 6.0 mmol) and DMA (4 mL) was microwave-irradiated at 150° C. for 1 h. 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, NH, 90:10 hexane/EtOAc to 50:50 hexane/EtOAc) to give a yellow solid. The solid was purified by crystallization from EtOAc/heptane to give the title compound (431 mg, 31%) as a yellow solid:

Workup

  1. customwas microwave-irradiated at 150° C. for 1 h
  2. extractionThe organic materials were extracted with EtOAc
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customAfter removal of the solvent at reduced pressure
  7. customthe residue was purified by column chromatography (Purif, NH, 90:10 hexane/EtOAc to 50:50 hexane/EtOAc)
  8. customto give a yellow solid
  9. customThe solid was purified by crystallization from EtOAc/heptane

Sources & evidence

ORD record
ord-b8020e7ea08346d59de7643b95f2dfaa
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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