Imidazole → HCID 57815179, compound

HRID 1510672Notes

Reaction equation

HRID 1510672 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:25])[N:16]2[CH2:19][CH:20]2[O:24][CH2:23][CH2:22][O:21]2)=[N:11][CH:10]=1.C(Cl)(Cl)Cl>CN(C)C=O.[Cu]=O.O>[O:24]1[CH2:23][CH2:22][O:21][CH:20]1[CH2:19][N:16]1[C:17]2[C:12](=[N:11][CH:10]=[C:9]([N:3]3[CH:7]=[CH:6][N:5]=[CH:4]3)[CH:18]=2)[CH:13]=[CH:14][C:15]1=[O:25]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 6212ChloroformHCID 24758Sodium hydrideHCID 578153037-bromo-1-(1,3-dioxolan-2-ylmethyl)-1,5-naphthyridin-2(1H)-one

Product 1

HCID 57815179HCID 57815179, compoundYield 62.6%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 77 mg of sodium hydride in 2 mL of N,N-dimethylformamide, 0.13 g of imidazole was added, and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture, 0.20 g of 7-bromo-1-((1,3-dioxolan-2-yl)methyl)-1,5-naphthyridin-2(1H)-one was added dividedly, and then 18 mg of copper (II) oxide was added thereto. The reaction mixture was stirred at 135 to 140° C. for 30 minutes. The reaction mixture was cooled to room temperature, then chloroform and water were added thereto, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. To the resultant residue, a mixed solvent of diethyl ether: ethyl:acetate (3:1) was added, and the solid was filtered off to obtain 0.12 g of 1-((1,3-dioxolan-2-yl)methyl)-7-(1H-imidazol-1-yl)-1,5-naphthyridin-2(1H)-one as a yellow solid.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at 135 to 140° C. for 30 minutes
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with chloroform
  6. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionTo the resultant residue, a mixed solvent of diethyl ether: ethyl:acetate (3:1) was added
  9. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-71a147ff8b234f018a0b8acc222c7710
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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