HCID 15372233, compound → HCID 22723987, compound

HRID 2086856Notes

Reaction equation

HRID 2086856 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11](/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30](=O)[C:31](O)=[O:32])[CH:24]=1>C(O)C>[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][C:30]2[C:31](=[O:32])[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11](/[CH:15]=[CH:16]/[C:17]4[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=4)[CH:10]=3)[C:3]3[N:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 15372233HCID 15372233, compoundHCID 22724193HCID 22724193, compound

Product 1

HCID 22723987HCID 22723987, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-2-[3-[(E)-2-(4-pyridyl)vinyl]phenylamino]pyridine (575 mg) and 3-(3-pyridyl)pyruvic acid (0.37 g) in ethanol (10 ml) was stirred under reflux for 1.5 hours. After evaporation of the solvent, the residue was chromatographed on silica gel column (chloroform-methanol, 9:1) and crystallized from ethanol to give 2-(3-pyridylmethyl)-4-[3-[(E)-2-(4-pyridyl)vinyl]phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (395 mg)

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customAfter evaporation of the solvent
  3. customthe residue was chromatographed on silica gel column (chloroform-methanol, 9:1)
  4. customcrystallized from ethanol

Sources & evidence

ORD record
ord-c2b1ef7c33694a2a8062c2a0c7fbbcf0
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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