HCID 67455752, compound → HCID 49771644, compound

HRID 639594Notes

Reaction equation

HRID 639594 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[C:14]([CH3:17])[N:13]=[C:12]([N:18](CC3C=CC=CC=3)CC3C=CC=CC=3)[C:11]=2[NH:10][C:9]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:18][C:12]1[C:11]2[NH:10][C:9](=[O:33])[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]=2[CH:15]=[C:14]([CH3:17])[N:13]=1

Participants

4

Reactant 1

HCID 67455752HCID 67455752, compound

Product 1

HCID 49771644HCID 49771644, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

1-Benzyl-4-dibenzylamino-6-methyl-1,3-dihydro-imidazo[4,5-c]pyridin-2-one (34 mg, 0.08 mmol) was suspended in ethanol (5 mL) and hydrogenated over 10% Pd(OH)2 (7 mg) at room temperature, 60 psi for 6 hours. The reaction mixture was filtered through a short plug of Arbocel and the filtrate was then evaporated in vacuo to an opaque gum. The gum was dissolved in methanol and preabsorbed onto silica gel and was then purified by column chromatography, eluting with 5% methanol in EtOAc. Appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid, 7 mg.

Workup

  1. filtrationThe reaction mixture was filtered through a short plug of Arbocel
  2. customthe filtrate was then evaporated in vacuo to an opaque gum
  3. dissolutionThe gum was dissolved in methanol
  4. custompreabsorbed onto silica gel
  5. customwas then purified by column chromatography
  6. washeluting with 5% methanol in EtOAc
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-5aca39d71af14b5c85f88187a2372ad5
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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