Glyoxal → 7-[1,2,4]Triazin-3-yl-imidazo[1,2-a]pyridine

HRID 2400356Notes

Reaction equation

HRID 2400356 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([C:10]([NH:12][NH2:13])=[NH:11])=[CH:6][C:5]=12.[CH:14]([CH:16]=O)=O>C(O)C>[N:13]1[CH:16]=[CH:14][N:11]=[C:10]([C:7]2[CH:8]=[CH:9][N:4]3[CH:3]=[CH:2][N:1]=[C:5]3[CH:6]=2)[N:12]=1

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 178512584HCID 178512584, compound

Product 1

HCID 689842287-[1,2,4]Triazin-3-yl-imidazo[1,2-a]pyridineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To half the material from step d (ca. 2.3 mmol) was added glyoxal (40% in water, 1 ml) and ethanol (15 ml) and the mixture heated to 100 deg C. After 1 hour the reaction was allowed to cool and was concentrated in vacuo. Water and dichloromethane was added and the mixture filtered under suction. The organic liquors were discarded and the aqueous layer was basified with 2N sodium hydroxide solution. To this was added dichloromethane and the mixture was again filtered under suction. The dichloromethane layer was separated and concentrated to furnish 289 mg of a yellow solid (80% clean). MS: [M+H]+198

Workup

  1. temperaturethe mixture heated to 100 deg C
  2. temperatureto cool
  3. concentrationwas concentrated in vacuo
  4. additionWater and dichloromethane was added
  5. filtrationthe mixture filtered under suction
  6. additionTo this was added dichloromethane
  7. filtrationthe mixture was again filtered under suction
  8. customThe dichloromethane layer was separated
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2367ad7f05f946268ed91ae7f1029057
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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