Methanol → HCID 135848081, compound

HRID 498028Notes

Reaction equation

HRID 498028 reaction equation
CO.[O:3]1CCCC1.[CH3:8][C:9]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([S:23][CH3:24])[CH:18]=3)[NH:13][C:12]=2[N:11]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[N:10]=1.I([O-])(=O)(=O)=O.[Na+]>O>[CH3:8][C:9]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([S:23]([CH3:24])=[O:3])[CH:18]=3)[NH:13][C:12]=2[N:11]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[N:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 135848121HCID 135848121, compound

Product 1

HCID 135848081HCID 135848081, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution in a mixed solvent of methanol (40 mL), tetrahydrofuran (10 mL) and water (10 mL) of 3-methyl-6-(methylsulfanyl)-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one (1.00 g, 3.10 mmol) and sodium periodate (0.66 g, 3.10 mmol) was heated under reflux for 2 hours. The solution was allowed to cool to room temperature, and concentrated under reduced pressure. The residue was poured into water, and the organic matter was extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform to chloroform:methanol=98:2) to give the title compound (0.63 g, 61% yield).

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was poured into water
  4. extractionthe organic matter was extracted with chloroform
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography (chloroform to chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-b5019c3a9c654b498ff42b2c01f0ea1f
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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