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

HRID 2086818Notes

Reaction equation

HRID 2086818 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-7d72e203936f450599799f6fdb66e4d8
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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