Ethanol → HCID 67278252, compound

HRID 1696246Notes

Reaction equation

HRID 1696246 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:12]2=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=[C:11]2[N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=2)[C:9]1=[O:30].C(O)C.[Cl-].[NH4+]>[Fe].O>[NH2:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][N:10]1[C:11]2[C:12](=[C:13]3[CH:19]=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[N:8]([C@H:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]2[CH3:1])[C:9]1=[O:30]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 67277272HCID 67277272, compound

Product 1

HCID 67278252HCID 67278252, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a solution of rel-1-[(1S,2R)-2-methylcyclohexyl]-3-(3-nitrobenzyl)-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (150 mg) in a mixed solution of ethanol (1.5 mL) and water (0.45 mL) were added iron powder (62 mg) and ammonium chloride (10 mg). The solution was refluxed for 3 hours. After cooling to ambient temperature, the precipitate was filtered through a pad of Celite. After concentration under reduced pressure, the residue was extracted with chloroform and washed with water and dried over MgSO4. Concentration under reduced pressure to give 3-(3-aminobenzyl)-1-[(1S,2R)-2-methylcyclohexyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]-pyridin-2(1H)-one (139 mg) as a white powder.

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. filtrationthe precipitate was filtered through a pad of Celite
  3. concentrationAfter concentration under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-819c244ff13941fab69f189b16c6981e
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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