Sodium ethoxide → 9,10-Dihydro-7H-imidazo[1′,2′:1,2]imidazo[4,5-c]-1,5-naphthyridine

HRID 415563Notes

Reaction equation

HRID 415563 reaction equation
[O-]CC.[Na+].CS([C:9]1[N:10]([CH2:22][CH2:23][NH:24]C(=O)OC(C)(C)C)[C:11]2[C:20]3[N:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:21]=1)(=O)=O>C(O)C>[N:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[C:11]1[N:10]3[CH2:22][CH2:23][NH:24][C:9]3=[N:21][C:12]=1[CH:13]=[N:14]2

Participants

4

Reactant 2

HCID 2723922Sodium ethoxide3×HCID 66619925HCID 66619925, compound

Product 1

HCID 1363428459,10-Dihydro-7H-imidazo[1′,2′:1,2]imidazo[4,5-c]-1,5-naphthyridineYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (4.2 g, 61 mmol) was added in one portion to a solution of tert-butyl 2-[2-(methylsulfonyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]ethylcarbamate (20 g, 50 mmol) in ethanol (200 mL), and the resulting mixture was heated at reflux for four hours. Analysis by LC/MS indicated that no reaction had taken place, and additional sodium ethoxide (4.2 g, 61 mmol) was added. The mixture was heated at reflux overnight. Analysis by LC/MS indicated the presence of starting material, and a solution of sodium ethoxide (21% in ethanol, 150 mL) was added to the mixture. The reaction was heated at reflux for two hours and then concentrated under reduced pressure. Water was added, and the mixture was extracted with dichloromethane. A precipitate formed in the aqueous layer; the precipitate was isolated by filtration and washed with water to provide 7.3 g of 9,10-dihydro-8H-imidazo[1′,2′:1,2]imidazo[4,5-c][1,5]naphthyridine as a white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for four hours
  3. additionwas added
  4. temperatureThe mixture was heated
  5. temperatureat reflux overnight
  6. temperatureThe reaction was heated
  7. temperatureat reflux for two hours
  8. concentrationconcentrated under reduced pressure
  9. additionWater was added
  10. extractionthe mixture was extracted with dichloromethane
  11. customA precipitate formed in the aqueous layer
  12. customthe precipitate was isolated by filtration
  13. washwashed with water

Sources & evidence

ORD record
ord-2eb5058a62a846b18a2dbd0e09687510
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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