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Water → HCID 178446132, compound

HRID 730008
Notes
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Reaction equation

HRID 730008 reaction equation
[C:1]([C:5]1[NH:9][C:8]([C:10]2[N:15]=[C:14]([NH:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]([N+:22]([O-])=O)=[CH:12][CH:11]=2)=[C:7]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:32]#[C:33]Br.C(OCC)(=O)C.O>[Pd].C(O)C.CO.C(Cl)Cl>[NH3:6].[C:1]([C:5]1[NH:6][C:7]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[C:8]([C:10]2[N:15]=[C:14]3[N:16]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:33]([NH2:32])=[N:22][C:13]3=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10476Cyanogen BromideHCID 68867957HCID 68867957, compound

Product 2

HCID 222AmmoniaHCID 178446132HCID 178446132, compoundYield 74.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Stir a suspension of {6-[2-tert-Butyl-5-(4-fluoro-phenyl)-3H-imidazol-4-yl]-3-nitro-pyridin-2-yl}-(2,2-dimethylpropyl)-amine (426 mg, 1.0 mmol) and 10% palladium on carbon (85 mg) in 100% ethanol under hydrogen from a balloon overnight. Filter the suspension through a 0.2 μm syringe filter and concentrate under reduced pressure. Dissolve the residue in 10% aqueous ethanol and treat at room temperature with cyanogen bromide (80 mg, 0.75 mmol, 1.5 equiv). When the reaction is complete, quench the reaction with saturated aqueous NaHCO3. Add ethyl acetate and water to dissolve all solids. Wash the organic layer once with saturated aqueous NaHCO3, once with saturated aqueous NaCl, dry with Na2SO4, filter, and concentrate under reduced pressure. Subject the residue to medium pressure silica gel chromatography eluting with 50% ethyl acetate/CH2Cl2 then with a gradient of 1.5-3.5% (2M ammonia in MeOH)/CH2Cl2) to provide 5-[2-tert-butyl-5-(4-fluoro-phenyl)-1H-imidazol-4-yl]-3-(2,2-dimethyl-propyl)-3H-imidazo[4,5-b]pyridin-2-ylamine as a brown foam (156 mg, 74% yield).

Workup

  1. filtrationFilter the suspension through a 0.2 μm syringe
  2. filtrationfilter
  3. concentrationconcentrate under reduced pressure
  4. dissolutionDissolve the residue in 10% aqueous ethanol
  5. customquench
  6. customthe reaction with saturated aqueous NaHCO3
  7. washWash the organic layer once with saturated aqueous NaHCO3
  8. dry with materialonce with saturated aqueous NaCl, dry with Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate under reduced pressure
  11. washeluting with 50% ethyl acetate/CH2Cl2

Sources & evidence

ORD record
ord-c2fe895bf56e4317a1c991fd8b31d2be
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582652B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes