HCID 66816724, compound → HCID 59846231, compound

HRID 1697100Notes

Reaction equation

HRID 1697100 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:22](=[O:31])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:6]([N:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][N:15]=2)=O)[CH:7]=1>CO.C([O-])([O-])=O.[K+].[K+]>[CH2:24]([C:23]1[C:22](=[O:31])[C:5]2[C:6](=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:8]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:9]=1[C:11]1[O:12][CH:13]=[CH:14][N:15]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 66816724HCID 66816724, compound

Product 1

HCID 59846231HCID 59846231, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 11430Potassium CarbonateSolvent

Procedure

Oxazole-2-carboxylic acid [5-chloro-2-(3-phenyl-propionyl)-phenyl]-phenyl-amide (387 mg) was dissolved in dry MeOH (20 mL) and K2CO3 (100 mg), and heated at reflux for 1.5 h. The product was then cooled, the solvent evaporated, and the residue chromatographed (0-30% MeOH/DCM) to provide 3-benzyl-7-chloro-2-oxazol-2-yl-1-phenyl-1H-quinolin-4-one (Compound 140, 233 mg). mp=219.0-220.0° C.

Workup

  1. temperatureat reflux for 1.5 h
  2. temperatureThe product was then cooled
  3. customthe solvent evaporated
  4. customthe residue chromatographed (0-30% MeOH/DCM)

Sources & evidence

ORD record
ord-c0d479f456204f49915bd7c2d6e879ff
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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