Water → HCID 178524348, compound

HRID 1822207Notes

Reaction equation

HRID 1822207 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1)#N.S(=O)(=O)(O)[OH:32].[OH2:36]>CS(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([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:7][CH:8]=1)([OH:32])=[O:36]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 178509734HCID 178509734, compound

Product 1

HCID 178524348HCID 178524348, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-[2-(4-cyanophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (100 mg, 0.26 mmol, prepared in Example 12) in DMSO (2 ml) was added 50% sulfuric acid (2 ml) and the mixture was heated under reflux for 2 hours. To the resultant reaction mixture was added water, and precipitates were filtered off, and dried to give 3-[2-(4-carboxyphenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (107 mg, quantitative yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customTo the resultant reaction mixture
  4. customprecipitates
  5. filtrationwere filtered off
  6. customdried

Sources & evidence

ORD record
ord-56dd421d87564571a2ff7257166747a0
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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