Ethylenediamine → HCID 68828573, compound

HRID 1986477Notes

Reaction equation

HRID 1986477 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:48]1[CH:49]=[C:50]2[C:55](=[CH:56][CH:57]=1)[N:54]=[C:53]([CH2:58][CH:59]([CH3:61])[CH3:60])[C:52]([C:62]#[N:63])=[C:51]2[C:64]1[CH:69]=[CH:68][C:67]([CH3:70])=[CH:66][CH:65]=1.[CH2:71]([NH2:74])[CH2:72][NH2:73].CC(C)([O-])C.[Na+].[C:81](OC(OC(C)(C)C)=O)([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[C:62]([C:52]1[C:53]([CH2:58][CH:59]([CH3:61])[CH3:60])=[N:54][C:55]2[C:50]([C:51]=1[C:64]1[CH:69]=[CH:68][C:67]([CH3:70])=[CH:66][CH:65]=1)=[CH:49][C:48]([NH:73][CH2:72][CH2:71][NH:74][C:81](=[O:82])[O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[CH:57][CH:56]=2)#[N:63]

Participants

8

Reactant 5

HCID 3301EthylenediamineHCID 90495Di-tert-butyl dicarbonateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 51050239HCID 51050239, compound

Product 1

HCID 68828573HCID 68828573, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

Palladium acetate (0.030 g, 0.13 mmol) and racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.25 g, 0.40 mmol) were added to toluene (20 ml) under a nitrogen atmosphere and the mixture was stirred at 40° C. for 30 min. The reaction mixture was cooled to room temperature and 6-bromo-2-isobutyl-4-(4-methylphenyl)quinoline-3-carbonitrile (1.0 g, 2.6 mmol), ethylenediamine (0.44 ml, 6.6 mmol) and sodium tert-butoxide (0.35 g, 3.7 mmol) were added. The mixture was stirred under a nitrogen atmosphere at 80° C. for 2 hrs. The reaction mixture was cooled and partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate. The aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, and the mixture was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in tetrahydrofuran (100 ml). Di-tert-butyl dicarbonate (0.73 ml, 3.2 mmol) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give tert-butyl 2-{[3-cyano-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]amino}ethylcarbamate (0.85 g, yield 70%) as a pale-yellow powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringThe mixture was stirred under a nitrogen atmosphere at 80° C. for 2 hrs
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe mixture was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. dissolutionthe residue was dissolved in tetrahydrofuran (100 ml)
  10. stirringthe mixture was stirred at room temperature for 1 hr
  11. concentrationThe reaction mixture was concentrated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6c020baeecd34194950e3befcb5f87d0
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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