HCID 11379002, compound → HCID 178513055, compound

HRID 898815Notes

Reaction equation

HRID 898815 reaction equation
C[O:2][C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)=O.CS(O)(=O)=O.FC1C=CC=CC=1C1OC(C([NH:36][C:37]([NH2:39])=[NH:38])=O)=CC=1>CO.[Cl-].[Na+].O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[O:6][C:5]([C:3]([NH:38][C:37]([NH2:39])=[NH:36])=[O:2])=[CH:9][CH:8]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 11379002HCID 11379002, compoundHCID 178505355HCID 178505355, compound

Product 1

HCID 178513055HCID 178513055, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-(4-fluorophenyl)furan-2-carboxylic acid methyl ester (220 mg, 1.0 mmol) was dissolved in methanol (4 ml), to which 2 M guanidine solution (3.0 ml, 6.0 mmol) prepared in Example 1 was added, and the mixture was heated at reflux for 12 hours. After completion of the reaction, the solution was added with saturated brine (20 ml) and extracted with ethyl acetate (30 ml×3). The organic layer was washed with 10% brine, dried over anhydrous magnesium sulfate (MgSO4), and concentrated in vacuo. The residue was purified by silica gel column chromatography (5% methanol/dichloromethane), to give 127 mg of a title compound (yield: 51%).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 12 hours
  4. customAfter completion of the reaction
  5. extractionextracted with ethyl acetate (30 ml×3)
  6. washThe organic layer was washed with 10% brine
  7. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-df06d6e6b2ca4bd898935427db93b9e9
Source dataset
uspto-grants-2008_04
Patent number
US07351843B2

Reaction notes

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