Ethylenediamine → HCID 178510687, compound

HRID 2376742Notes

Reaction equation

HRID 2376742 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[C:8]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[NH:4][N:3]=1.[Cu](C#N)[C:32]#[N:33].C(N)CN>CN1CCCC1=O>[F:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[C:8]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:7]([C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[N:6]=[C:5]3[NH:4][N:3]=[C:2]([C:32]#[N:33])[C:10]=23)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 178418260HCID 178418260, compoundHCID 178505545HCID 178505545, compound

Product 1

HCID 178510687HCID 178510687, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a volumetric flask, 3-bromo-4,6-bis(4-fluorophenyl)-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.20 g, 0.4 mmol, obtained in example 64), copper cyanide (I) (0.05 g, 0.6 mmol) and anhydrous 1-methyl-2-pyrrolidone (1 mL) were introduced under argon atmosphere and heated to reflux for 2 h. This was poured into a 10% aqueous solution of ethylendiamine (4 mL) and extracted with CHCl3. Brine was added to the aqueous phase and it was extracted with EtOAc. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford the title compound in a solid form (yield: quantitative).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. extractionextracted with CHCl3
  4. additionBrine was added to the aqueous phase and it
  5. extractionwas extracted with EtOAc
  6. dry with materialThe combined organic phases were 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-7a451683a6b444899e36927a3b708753
Source dataset
uspto-grants-2008_12
Patent number
US07468376B2

Reaction notes

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