Hydrogen Bromide → HCID 178514896, compound

HRID 1822232Notes

Reaction equation

HRID 1822232 reaction equation
C[O:2][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.Br.O>C(O)(=O)C>[OH:2][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

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 962WaterHCID 178489936HCID 178489936, compound

Product 1

HCID 178514896HCID 178514896, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (100 mg, 0.26 mmol, prepared in Example 21) in acetic acid (1 ml) was added 47% hydrogen bromide (44 μl), and the mixture was heated under reflux. After additional 47% hydrogen bromide (144 μl) was added, the mixture was heated under reflux overnight. The reaction mixture was admixed with water, and filtered to give precipitates which were dried to afford 3-(4-hydroxybenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]-naphthyridin-4 (5H)-one (92.1 mg, 96%).

Workup

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

Sources & evidence

ORD record
ord-29bce7929f394a2990bac817ac858aac
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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