Water → HCID 178524376, compound

HRID 1822245Notes

Reaction equation

HRID 1822245 reaction equation
[CH2:1]([C:8]1[C:12]2[C:13](=[O:29])[N:14]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#N)[CH:22]=3)[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]=2[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:31].[OH2:35]>CS(C)=O>[CH2:1]([C:8]1[C:12]2[C:13](=[O:29])[N:14]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([OH:31])=[O:35])[CH:22]=3)[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]=2[NH:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 178509827HCID 178509827, compound

Product 1

HCID 178524376HCID 178524376, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-benzyl-5-(3-cyanophenyl)-1H-pyrazolo [4,3-c][1,8]naphthyridin-4 (5H)-one (120 mg, 0.32 mmol, prepared in Example 53) in DMSO (15 ml) was added 50% sulfuric acid (5 ml), and the mixture was heated under reflux for 2.5 hours. The reaction mixture was admixed with water, and filtered to give precipitates which were dried to afford 3-benzyl-5-(3-carboxyphenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (73 mg, 58%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. filtrationfiltered
  4. customto give
  5. customprecipitates which
  6. customwere dried

Sources & evidence

ORD record
ord-8334f24231b84bab9eff08acbc16f085
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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