HCID 10274305, compound → 1-[(2S,3R)-2-hydroxy-5-(6-quinolyloxy)-3-pentyl]imidazole-4-carboxamide

HRID 1829802Notes

Reaction equation

HRID 1829802 reaction equation
C([O:8][C@H:9]([C@H:11]([N:25]1[CH:29]=[C:28]([C:30]([NH2:32])=[O:31])[N:27]=[CH:26]1)[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[CH3:10])C1C=CC=CC=1>C1CCCCC=1.C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C@H:9]([C@H:11]([N:25]1[CH:29]=[C:28]([C:30]([NH2:32])=[O:31])[N:27]=[CH:26]1)[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[CH3:10]

Participants

5

Reactant 1

HCID 10274305HCID 10274305, compound

Product 1

HCID 99025151-[(2S,3R)-2-hydroxy-5-(6-quinolyloxy)-3-pentyl]imidazole-4-carboxamideYield 86.8%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

To a solution of 1-[(2S,3R)-2-benzyloxy-5-(6-quinolyloxy)-3-pentyl]imidazole-4-carboxamide (58 mg, 0.135 mmol) in cyclohexene (2.5 ml) and ethanol (5 ml) was added 20% palladium hydroxide on carbon (50 mg). The resulting mixture was stirred at reflux for 8 h. After cooling to room temperature, the mixture was filtered through Celite and washed with ethanol. The filtrate was concentrated in vacuo and then the residue was purified by silica gel (1.5 g) chromatography eluted with chloroform/methanol (50:1 to 10:1) to give 1-[(2S,3R)-2-hydroxy-5-(6-quinolyloxy)-3-pentyl]imidazole-4-carboxamide (2) (39.8 mg, 86.8%).

Workup

  1. temperatureat reflux for 8 h
  2. filtrationthe mixture was filtered through Celite
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel (1.5 g) chromatography
  6. washeluted with chloroform/methanol (50:1 to 10:1)

Sources & evidence

ORD record
ord-409ee31646c04a8ba8ae6bcb7aaee254
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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