HCID 15372233, compound → 2-(3-pyridylmethyl)-3-oxo-4-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenyl]-3,4-dihydropyrido[2,3-b]pyrazine

HRID 1953415Notes

Reaction equation

HRID 1953415 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:18]=[N:19][CH:20]=[C:21](/[CH:23]=[CH:24]/[C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[CH:22]=3)[CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][C:38](=O)[C:39](O)=[O:40])[CH:32]=1>C(O)C>[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][C:38]2[C:39](=[O:40])[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11](/[CH:15]=[CH:16]/[C:17]4[CH:18]=[N:19][CH:20]=[C:21](/[CH:23]=[CH:24]/[C:25]5[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=5)[CH:22]=4)[CH:10]=3)[C:3]3[N:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH:32]=1

Participants

4

Reactant 2

HCID 15372233HCID 15372233, compoundHCID 23298118HCID 23298118, compound

Product 1

HCID 232981212-(3-pyridylmethyl)-3-oxo-4-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenyl]-3,4-dihydropyrido[2,3-b]pyrazineYield 60.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-amino-2-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenylamino]pyridine (260 mg) and 3-pyridylpyruvic acid (121 mg) in ethanol (5 ml) was stirred under reflux for 5 hours. After removal of the solvent, the residue was chromatographed on silica gel column (chloroform-methanol, 9:1) and crystallized from methanol to give 2-(3-pyridylmethyl)-3-oxo-4-[3-[(E)-2-[5-[(E)-2-(4-pyridyl)vinyl]pyridin-3-yl]vinyl]phenyl]-3,4-dihydropyrido[2,3-b]pyrazine (208 mg).

Workup

  1. temperatureunder reflux for 5 hours
  2. customAfter removal of the solvent
  3. customthe residue was chromatographed on silica gel column (chloroform-methanol, 9:1)
  4. customcrystallized from methanol

Sources & evidence

ORD record
ord-c9709a5ef5af4047a19b32083d85a2d4
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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