2-Aminopyridine → HCID 21265805, compound

HRID 566257Notes

Reaction equation

HRID 566257 reaction equation
Br[CH:2]([CH3:19])[C:3](=O)[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:6].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(=O)([O-])O.[Na+]>COCCOC>[CH3:19][C:2]1[N:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]2=[N:20][C:3]=1[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:6]

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 516892Sodium BicarbonateHCID 21265818HCID 21265818, compound

Product 1

HCID 21265805HCID 21265805, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Nitrobenzyl 4-bromo-3-oxopentanoate (1.02 g) and 2-aminopyridine (436 mg) were dissolved in 1,2-dimethoxyethane (20 ml). The solution was heated for 15 hours under reflux. The reaction mixture was concentrated, to which were added 1N HCl (10 ml) and ethyl acetate (10 ml). The mixture was shaken and left standing to form two layers. To the aqueous layer was added sodium hydrogencarbonate to adjust its pH to 7, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, which was concentrated under reduced pressure. The concentrate was purified by means of a column chromatography (carrier: silica gel, 30 g, developing: ethyl acetate) to afford the title compound (0.27 g).

Workup

  1. temperatureThe solution was heated for 15 hours
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated, to which
  4. additionwere added 1N HCl (10 ml) and ethyl acetate (10 ml)
  5. waitleft
  6. customto form two layers
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate, which
  9. concentrationwas concentrated under reduced pressure
  10. customThe concentrate was purified by means of a column chromatography (carrier: silica gel, 30 g, developing: ethyl acetate)

Sources & evidence

ORD record
ord-850ab57f328641c18d7cc17303b27973
Source dataset
uspto-grants-2001_01
Patent number
US06174877B1

Reaction notes

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