Water → HCID 178524349, compound

HRID 1822229Notes

Reaction equation

HRID 1822229 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[C:15]3[C:16](=[O:30])[N:17]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:18]4[N:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:14]=3[NH:13][N:12]=2)[CH:6]=[CH:7][CH:8]=1)#N.S(=O)(=O)(O)[OH:32].[OH2:36]>CS(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[C:15]3[C:16](=[O:30])[N:17]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:18]4[N:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:14]=3[NH:13][N:12]=2)[CH:6]=[CH:7][CH:8]=1)([OH:32])=[O:36]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 178509741HCID 178509741, compound

Product 1

HCID 178524349HCID 178524349, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-[2-(3-cyanophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (300 mg, 0.77 mmol, prepared in Example 18) in DMSO (30 ml) was added 50% sulfuric acid (15 ml), and the mixture was heated under reflux overnight. The reaction mixture was admixed with water, and filtered to give precipitates which were dried to afford 3-[2-(3-carboxyphenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (87 mg, 28%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationfiltered
  4. customto give
  5. customprecipitates which
  6. customwere dried

Sources & evidence

ORD record
ord-ff8f2e65abf0414db42e95168cd5aeeb
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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