Sodium hydride → 5-[4-(Amino)butoxy]imidazo[1,2-a]pyridine

HRID 5430

Reaktionsgleichung

Reaktionsgleichung von HRID 5430
[H-].[Na+].Cl[C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].C(OC([O-])=O)(OC(C)(C)C)=O>CN(C=O)C>[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 258684-Amino-1-butanolHCID 109537225-Chloroimidazo[1,2-A]pyridineHCID 22064466Tert-butyldicarbonate

Produkt 1

HCID 233629795-[4-(Amino)butoxy]imidazo[1,2-a]pyridineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of 60% sodium hydride (oily; 1.32 g, 33 mmloes) in DMF (60 ml) was added a solution of 5-chloroimidazo[1,2-a]pyridine (4.59 g, 30.1 mmoles) and 4-aminobutanol (2.68 g, 30.1 mmoles) in DMF (60 ml) at room temperature with stirring and the mixture was stirred at the same temperature for 5 hours. Tert-butyl dicarbonate (9.83 g, 45 mmoles) was added to the reaction solution, which was stirred at room temperature for 13 hours. After the solvent was distilled off, water was added to the residue, which was extracted with ether twice, washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was dissolved in methanol (20 ml), followed by the addition of conc. hydrochloric acid (20 ml) and stirring at room temperature for 1 hour. After the solvent was distilled off, chloroform was added to the residue, which was washed with 3N NaOH. After drying over anhydrous potassium carbonate, the solvent was distilled off. The residue was purified by column chromatography (eluent: methanol/chloroform=1:5) to obtain 2.53 g of the desired product (40.9%, light brown oily product).

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 5 hours
  2. stirringwas stirred at room temperature for 13 hours
  3. distillationAfter the solvent was distilled off
  4. additionwater was added to the residue, which
  5. extractionwas extracted with ether twice
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. dissolutionThe residue was dissolved in methanol (20 ml)
  10. additionfollowed by the addition of conc. hydrochloric acid (20 ml)
  11. stirringstirring at room temperature for 1 hour
  12. distillationAfter the solvent was distilled off
  13. additionchloroform was added to the residue, which
  14. washwas washed with 3N NaOH
  15. dry with materialAfter drying over anhydrous potassium carbonate
  16. distillationthe solvent was distilled off
  17. customThe residue was purified by column chromatography (eluent: methanol/chloroform=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-0f285cb157234f1fa10f07e2d940a71c
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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