Ethanol → HCID 131727763, compound

HRID 1435957Notes

Reaction equation

HRID 1435957 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][NH:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([O:32][CH3:33])[CH:26]=2)[CH:6]=[CH:5][C:4]=1[OH:34].C(OC([N:42]1[CH2:47][CH2:46][C:45]2[N:48]([CH2:57][CH2:58][CH2:59][NH:60]C(OCC3C=CC=CC=3)=O)[C:49]([C:51]3[CH:56]=[CH:55][N:54]=[CH:53][CH:52]=3)=[CH:50][C:44]=2[C:43]1=[O:71])=O)(C)(C)C.CCO>C1CCCCC=1.[Pd]>[CH3:33][O:32][C:27]1[CH:26]=[C:25]([CH2:24][NH:23][CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12][CH2:11][NH:10][CH2:9][C:7]2[CH:6]=[CH:5][C:4]([OH:34])=[C:3]([O:2][CH3:1])[CH:8]=2)[CH:30]=[CH:29][C:28]=1[OH:31].[NH2:60][CH2:59][CH2:58][CH2:57][N:48]1[C:45]2[CH2:46][CH2:47][NH:42][C:43](=[O:71])[C:44]=2[CH:50]=[C:49]1[C:51]1[CH:52]=[CH:53][N:54]=[CH:55][CH:56]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 131727765HCID 131727765, compound

Product 1

HCID 131727763HCID 131727763, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8079CyclohexeneSolvent

Procedure

DL-6-(3-benzyloxycarbonylamino-propyl)-4-oxo-2-pyridin-4-yl-1,4,6,7-tetrahydro-pyrrolo[3,2-c]pyridine-5-carboxylic acid tert-butyl ester (0.4 g) was dissolved in cyclohexene (10 mL) and absolute EtOH (20 mL), 10% Pd on carbon (0.2 g) was added and the mixture was refluxed for 1.5 hours. After filtration through celite and solvent evaporation under reduced pressure, the compound was treated with 4N HCl in dioxane (20 mL) for 2.5 hours at room temperature. The solution was concentrated and the residue treated with ethyl acetate. The precipitate was filtered, washed with little ethyl acetate and dried. The residue was dissolved in 4M HCl in dioxane and stirred for 4 hours at room temperature. The solution was concentrated and the title compound, as the dihydrochloride, was recovered as a yellowish solid (0.29 g, quantitative).

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. filtrationAfter filtration through celite and
  3. customsolvent evaporation under reduced pressure
  4. additionthe compound was treated with 4N HCl in dioxane (20 mL) for 2.5 hours at room temperature
  5. concentrationThe solution was concentrated
  6. additionthe residue treated with ethyl acetate
  7. filtrationThe precipitate was filtered
  8. washwashed with little ethyl acetate
  9. customdried
  10. dissolutionThe residue was dissolved in 4M HCl in dioxane
  11. concentrationThe solution was concentrated
  12. customthe title compound, as the dihydrochloride, was recovered as a yellowish solid (0.29 g, quantitative)

Sources & evidence

ORD record
ord-dad5e2785fff406f9c2fd2cefaa9910a
Source dataset
uspto-grants-2009_11
Patent number
US07618982B2

Reaction notes

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