HCID 68452390, compound → HCID 68454615, compound

HRID 272555Notes

Reaction equation

HRID 272555 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH:15][CH:16]1[CH2:20][CH2:19][N:18](CC3C=CC=CC=3)[CH2:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]>C(O)C.C(O)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH:15][CH:16]1[CH2:20][CH2:19][NH:18][CH2:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 68452390HCID 68452390, compound

Product 1

HCID 68454615HCID 68454615, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 2.8 g (7 mmol) 5-(1-benzyl-pyrrolidin-3-ylamino)-1H-indole-2-carboxylic acid ethyl ester in 180 ml ethanol and 20 ml acetic acid was hydrogenated over Pd/C for 24 h at room temperature. After filtration and evaporation the residue was taken up in 200 ml 10% NaHCO3 aq. and extracted with 150 ml dichloromethane (DCM). The aqueous phase was washed 7 times with 80 ml DCM each and the combined organic phases were dried over Na2SO4. After filtration and evaporation to dryness the residue was purified over Isolute® SPE (solid phase extraction) eluting with a gradient formed from DCM/2N NH3 in methanol to yield 1.05 g (74%) of the title compound and light brown crystals. MS (m/e): 274.3 (MH+, 100%).

Workup

  1. filtrationAfter filtration and evaporation the residue
  2. extractionextracted with 150 ml dichloromethane (DCM)
  3. washThe aqueous phase was washed 7 times with 80 ml DCM each and the combined organic phases
  4. dry with materialwere dried over Na2SO4
  5. filtrationAfter filtration and evaporation to dryness the residue
  6. customwas purified over Isolute® SPE (solid phase extraction)
  7. washeluting with a gradient
  8. customformed from DCM/2N NH3 in methanol

Sources & evidence

ORD record
ord-acfbb78807064f80b6c08f8f2a96cc33
Source dataset
uspto-grants-2008_11
Patent number
US07456174B2

Reaction notes

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