Water → HCID 178524332, compound

HRID 1822230Notes

Reaction equation

HRID 1822230 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([CH2:7][C:8]2[C:12]3[C:13](=[O:27])[N:14]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:15]4[N:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]=3[NH:10][N:9]=2)=[CH:5][CH:4]=1)#N.S(=O)(=O)(O)[OH:31].[OH2:35]>CS(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[C:12]3[C:13](=[O:27])[N:14]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:15]4[N:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]=3[NH:10][N:9]=2)=[CH:28][CH:29]=1)([OH:31])=[O:35]

Participants

5

Reactant 3

HCID 962Water3×HCID 1118Sulfuric AcidHCID 178509725HCID 178509725, compound

Product 1

HCID 178524332HCID 178524332, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 3-(4-cyanobenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (180 mg, 0.48 mmol, prepared in Example 31) in DMSO (18 ml) was added 50% sulfuric acid (10 ml), and the mixture was stirred at 140° C. After water (5 ml) was added, the mixture was heated under reflux, admixed with additional water (5 ml), and heated under reflux for totally 3 hours. The reaction mixture was admixed with water, and filtered to give precipitates which were dried to afford 3-(4-carboxybenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (106 mg, 56%).

Workup

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

Sources & evidence

ORD record
ord-717d1399a5844ba882e83ed4a40afd1e
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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