Potassium Hydroxide → HCID 178516485, compound

HRID 402732Notes

Reaction equation

HRID 402732 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[O:15][C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])=[C:13](C(OC)=O)[C:12]2=[O:29])=[CH:2]1.[OH-].[K+]>C(O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[C:12](=[O:29])[CH:13]=[C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[O:15]2)=[CH:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178498778HCID 178498778, compound

Product 1

HCID 178516485HCID 178516485, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (0.10 g, 0.25 mmol) of Example 101 in ethanol (4.0 mL), 50% potassium hydroxide solution (2.0 mL, 0.036 mol) was added at ambient temperature. The mixture was refluxed for 2 h. Cooled to ambient temperature, the solvent was removed under reduced pressure. Water was added to this residue, the mixture was washed with ethyl acetate then 1M hydrochloric acid was added to adjust pH to acidic, and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrate then purified by chromatography on silica gel(dichloromethane/methanol) to afford the titled compound as solid (0.012 g, y. 14%).

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customthe solvent was removed under reduced pressure
  3. additionWater was added to this residue
  4. washthe mixture was washed with ethyl acetate
  5. addition1M hydrochloric acid was added
  6. extractionthen extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrate
  9. customthen purified by chromatography on silica gel(dichloromethane/methanol)

Sources & evidence

ORD record
ord-43fa59873e23488e977b005b8602df45
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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