Water → HCID 178525175, compound

HRID 1822237Notes

Reaction equation

HRID 1822237 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[CH:33]=[CH:32][C:10]([CH2:11][C:12]2[C:16]3[C:17](=[O:31])[N:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:19]4[N:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[NH:14][N:13]=2)=[CH:9][CH:8]=1)=[O:5])C.S(=O)(=O)(O)O.O>CS(C)=O>[C:4]([CH2:6][C:7]1[CH:33]=[CH:32][C:10]([CH2:11][C:12]2[C:16]3[C:17](=[O:31])[N:18]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:19]4[N:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[NH:14][N:13]=2)=[CH:9][CH:8]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 178470662HCID 178470662, compound

Product 1

HCID 178525175HCID 178525175, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-(4-Ethoxycarbonylmethylbenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (110 mg, 0.25 mmol, prepared in Example 32) was dissolved in DMSO (3 ml) at 50° C., admixed with 50% sulfuric acid (2 ml) at 100° C., and then heated under reflux for 1 hour. The reaction mixture was admixed with water, and filtered to give precipitates which were dried to afford 3-(4-carboxymethylbenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (96 mg, 93%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. filtrationfiltered
  4. customto give
  5. customprecipitates which
  6. customwere dried

Sources & evidence

ORD record
ord-c2862ee908f144f19285c8c81a888c05
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

Loading…