Water → HCID 15486861, compound

HRID 1814061Notes

Reaction equation

HRID 1814061 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)(=O)=O)C=CC=CC=1.[OH-].[K+].O>CO>[CH3:22][S:19]([C:17]1[CH:18]=[C:13]2[CH:12]=[C:11]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[NH:10][C:14]2=[N:15][CH:16]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22504433HCID 22504433, compound

Product 1

HCID 15486861HCID 15486861, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound obtained in Example 5 (3) (3.8 mg) in methanol (0.5 ml), a 1N aqueous potassium hydroxide solution (2 ml) was added and the mixture was heated under reflux for 2 hours. After completion of the reaction, the reaction solution was poured into water, extracted with chloroform, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was poured into a phosphorate buffer (pH 7.0), extracted with dichloromethane, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (chloroform methanol=50:1) to obtain 2.4 mg of the desired product as a white powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter completion of the reaction
  4. extractionextracted with chloroform
  5. washwashed with a saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. additionThe residue was poured into a phosphorate buffer (pH 7.0)
  10. extractionextracted with dichloromethane
  11. washwashed with a saturated aqueous NaCl solution
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure
  15. customThe resulting residue was separated

Sources & evidence

ORD record
ord-6d390134edb54685b48a99f128668f7c
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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