HCID 23442386, compound → HCID 23442423, compound

HRID 2119644Notes

Reaction equation

HRID 2119644 reaction equation
[C:1]([C:9]1[CH:18]=[CH:17][C:16]2[NH:15][C:14]3[CH:19]=[N:20][N:21]([CH3:22])[C:13]=3[C:12](=[O:23])[C:11]=2[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[OH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:18]=[CH:17][C:16]2[NH:15][C:14]3[CH:19]=[N:20][N:21]([CH3:22])[C:13]=3[C:12](=[O:23])[C:11]=2[CH:10]=1

Participants

3

Reactant 1

HCID 23442386HCID 23442386, compound

Product 1

HCID 23442423HCID 23442423, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 7-benzoyl-1-methyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (EXAMPLE 36, step 1, 33 mg, 0.11 mmol) in phosphorus oxychloride (3 ml) was refluxed for 3 h. After evaporation, the residue was dissolved in ethyl acetate (20 ml) and washed with saturated aqueous sodium bicarbonate (20 ml). The water layer was extracted with ethyl acetate (20 ml×2) and the combined organic layer was dried over sodium sulfate. Removal of solvent gave an oily residue, which was purified by preparative thin layer chromatography developing with ethyl acetate/hexane (2:1) to afford 24 mg (69%) of the title compound as a white solid.

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  3. washwashed with saturated aqueous sodium bicarbonate (20 ml)
  4. extractionThe water layer was extracted with ethyl acetate (20 ml×2)
  5. dry with materialthe combined organic layer was dried over sodium sulfate
  6. customRemoval of solvent
  7. customgave an oily residue, which
  8. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-26b2791849a34076be977759fd1fa2b0
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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