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Acetic Acid → 4-[5-(4-fluorophenyl)-1-methyl-3-oxido-2-phenyl-1H-imidazol-4-yl]pyridin-2(1H)-one

HRID 23525
Notes
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Reaction equation

HRID 23525 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]([C:12]2[CH:17]=[CH:16][N:15]=C(F)C=2)=[N:10][OH:11])=[CH:4][CH:3]=1.[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:28][NH2:29].[C:30]([OH:33])(=O)[CH3:31]>C(Cl)Cl.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:29]([CH3:28])[C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N+:10]([O-:11])[C:9]=2[C:12]2[CH:17]=[CH:16][NH:15][C:30](=[O:33])[CH:31]=2)=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 6329MethylamineHCID 1363357801-(2-Fluoropyridin-4-yl)-2-(4-fluorophenyl)ethane-1,2-dione-1-oxime

Product 1

HCID 695576504-[5-(4-fluorophenyl)-1-methyl-3-oxido-2-phenyl-1H-imidazol-4-yl]pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 21226129
Dichloromethane methanol
Solvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 1-(4-fluorophenyl)-2-(2-fluoropyridin-4-yl)ethane-1,2-dione 2-oxime (Example 1, Step B) (400 mg, 1.52 mmol) in acetic acid (7.6 mL) was added benzaldehyde (170 μL, 1.68 mmol) followed by methylamine (144 μL, 40 wt. % in H2O, 1.68 mmol), and the mixture was heated for 41 hours at 100° C. It was cooled and acetic acid was removed in vacuo. The residue was taken up in H2O and was concentrated in vacuo two times. This was repeated with toluene to obtain crude residue. The crude residue was dissolved in a mixture of CH2Cl2/MeOH, filtered off solid (unreacted, hydrolyzed imidazole), and the solvent was removed in vacuo. The crude product was pre-absorbed on silica gel and purified by flash chromatography eluting with 5% MeOH/CH2Cl2 followed by 10% 2M NH3 in MeOH/CH2Cl2 to obtain 270 mg of the title compound.

Workup

  1. temperatureIt was cooled
  2. customacetic acid was removed in vacuo
  3. concentrationwas concentrated in vacuo two times
  4. customto obtain crude residue
  5. filtrationfiltered off solid (unreacted, hydrolyzed imidazole)
  6. customthe solvent was removed in vacuo
  7. customThe crude product was pre-absorbed on silica gel
  8. custompurified by flash chromatography
  9. washeluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1e70f435aee645cbb542fdc2092f5543
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852727B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes