Hydrogen Bromide → HCID 178514881, compound

HRID 1822233Notes

Reaction equation

HRID 1822233 reaction equation
C[O:2][C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[CH2:5][C:6]1[C:10]2[C:11](=[O:25])[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:9]=2[NH:8][N:7]=1.Br.O>C(O)(=O)C>[OH:2][C:3]1[CH:29]=[CH:28][CH:27]=[CH:26][C:4]=1[CH2:5][C:6]1[C:10]2[C:11](=[O:25])[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:9]=2[NH:8][N:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 962WaterHCID 178489437HCID 178489437, compound

Product 1

HCID 178514881HCID 178514881, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3-(2-methoxybenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (50 mg, 0.13 mmol, prepared in Example 22) in acetic acid (1 ml) was added 47% hydrogen bromide (0.5 ml), and the mixture was heated under reflux. After additional 47% hydrogen bromide (1 ml) and acetic acid (1 ml) was added, the mixture was heated under reflux for 2 days, then admixed with water, filtered to give precipitates which were dried to afford 3-(2-hydroxybenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]-naphthyridin-4 (5H)-one (31 mg, 64%).

Workup

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

Sources & evidence

ORD record
ord-02d43ebe9926428696aa3f3dc7014df2
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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