Water → 2-(2-Aminoethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

HRID 42593Notes

Reaction equation

HRID 42593 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:10](=[N:27][N:28]([CH2:30][CH2:31][N:32]4C(=O)C5=CC=CC=C5C4=O)[CH:29]=3)[N:11]=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.O.NN.O.CCOC(C)=O>CCO>[NH2:32][CH2:31][CH2:30][N:28]1[CH:29]=[C:9]2[C:10]([N:11]=[C:12]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[C:8]2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 670147764,6-Bis(4-fluorophenyl)-2-(2-phthalimidoethyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine

Product 1

HCID 670135732-(2-Aminoethyl)-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridineYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4,6-bis(4-fluorophenyl)-2-(2-phthalimidoethyl)-5-(4-pyridyl)pyrazolo[3,4-b]pyridine (0.09 g, 0.2 mmol, obtained in example 89) in EtOH (2 mL), hydrazine monohydrate (0.02 g, 0.3 mmol) was added and the mixture was heated to reflux for 3 h. A mixture of water and EtOAc was added. The phases were separated. The aqueous phase was extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using CHCl3-MeOH mixtures of increasing polarity as eluent, to afford 57 mg of the title compound (yield: 83%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h
  3. additionwas added
  4. customThe phases were separated
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe crude product obtained
  9. customwas purified by chromatography on silica gel
  10. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-f2384b4e9aee477da9a8929cd0362829
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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