4-Methyl-2-oxovaleric acid → HCID 22724447, compound

HRID 2230994Notes

Reaction equation

HRID 2230994 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:21][CH:22]([CH3:29])[CH2:23][C:24](=O)[C:25](O)=[O:26].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[C:11]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=[C:9]([N:8]2[C:25](=[O:26])[C:24]([CH2:23][CH:22]([CH3:29])[CH3:21])=[N:1][C:2]3[CH:7]=[CH:6][CH:5]=[N:4][C:3]2=3)[CH:10]=1

Participants

6

Reactant 4

HCID 704-Methyl-2-oxovaleric acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22724036HCID 22724036, compound

Product 1

HCID 22724447HCID 22724447, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-2-(3-biphenylylamino)pyridine (157 mg) and 4-methyl-2-oxopentanoic acid (94 mg) in ethanol (3 ml) was stirred under reflux for 2 hours. The mixture was cooled and then poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (hexane-ethyl acetate, 3:1) to give 4-(3-biphenylyl)-2-isobutyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (47 mg).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe mixture was cooled
  3. customThe organic phase was separated
  4. washwashed with aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel column (hexane-ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-ae62834692bf40148291c2b587d2dca1
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

Loading…