Oxaloacetic Acid → HCID 22724219, compound

HRID 2086819Notes

Reaction equation

HRID 2086819 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[O:23]=[C:24]([CH2:28][C:29](O)=O)C(O)=O.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[CH:18]1([O:17][C:11]2[CH:10]=[C:9]([N:8]3[C:24](=[O:23])[C:28]([CH3:29])=[N:1][C:2]4[CH:7]=[CH:6][CH:5]=[N:4][C:3]3=4)[CH:14]=[CH:13][C:12]=2[O:15][CH3:16])[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 970Oxaloacetic AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22724148HCID 22724148, compound

Product 1

HCID 22724219HCID 22724219, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-2-[(3-cyclopentyloxy-4-methoxyphenyl)amino]pyridine (180 mg) and 2-oxosuccinic acid (90 mg) in ethanol (4 ml) was stirred under reflux for 1.5 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 resultant solid was washed with ethanol to give 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-methyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (100 mg).

Workup

  1. temperatureunder reflux for 1.5 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. washThe resultant solid was washed with ethanol

Sources & evidence

ORD record
ord-6b7e698bc2634a5780c91aa559b40e27
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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