2-Aminopyridine → HCID 19347454, compound

HRID 1638174Notes

Reaction equation

HRID 1638174 reaction equation
Br.Br[CH:3]1[C:14](=[O:15])[C:7]2[N:8]3N=C[N:11]=[C:9]3S[C:6]=2[CH2:5][CH2:4]1.NC1[CH:22]=[CH:21][CH:20]=[CH:19]N=1>C(O)C>[CH:19]1[N:8]2[C:9](=[N:11][C:6]3[CH2:5][CH2:4][CH2:3][C:14](=[O:15])[C:7]=32)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 19347471HCID 19347471, compound

Product 1

HCID 19347454HCID 19347454, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromo-1,3-cyclohexadione (9.55 g) prepared in Example 1, Route 1 (A) and 2-aminopyridine (4.7 g) were dissolved into absolute ethanol (200 ml), and the reaction mixture was heated to reflux for 20 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved into water. The solution was neutralized with sodium carbonate, extracted with chloroform three times, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant:methylene chloride: acetonitrile=2:1) to give the titled compound (3.0 g, 32%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 20 hours
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved into water
  6. extractionextracted with chloroform three times
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluant:methylene chloride: acetonitrile=2:1)

Sources & evidence

ORD record
ord-6fee3701d53348d7aeb21e1810fa768c
Source dataset
uspto-grants-2000_03
Patent number
US06043373

Reaction notes

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