Chloroacetaldehyde → Imidazo[1,2-a]pyridin-5-amine

HRID 331112

Reaktionsgleichung

Reaktionsgleichung von HRID 331112
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[CH3:9][CH2:10]O.C(=O)(O)[O-].[Na+].ClCC=O>[Na+].[Cl-]>[N:1]1[CH:9]=[CH:10][N:3]2[C:4]([NH2:8])=[CH:5][CH:6]=[CH:7][C:2]=12

Komponenten

6

Edukt 4

HCID 33ChloroacetaldehydeHCID 702EthanolHCID 88612,6-DiaminopyridineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 327952Imidazo[1,2-a]pyridin-5-amineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5234Sodium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2,6-diaminopyridine (5.00 g, 45.8 mmol) in 1:1H2O:EtOH (10 mL) were added sodium bicarbonate (5.00 g, 59.5 mmol) and chloroacetaldehyde (4.31 g, 27.5 mmol). The reaction mixture was heated to 70° C. overnight, then cooled to rt, diluted with saturated aqueous NaCl (100 mL), and extracted with n-butanol (3×200 mL). The organic layers were combined, dried (MgSO4), and concentrated. The crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give imidazo[1,2-a]pyridin-5-ylamine (1.32 g, 22%). MS (ESI+): calcd for C7H7N3 m/z 133.06, found 134.1 (M+H)+. 1H NMR (d6-DMSO): 8.23-8.21 (m, 1H), 7.91 (d, J=1.3, 1H), 7.50 (dd, J=8.8, 7.4, 1H), 7.22 (d, J=8.8, 1H), 6.97 (br s, 2H), 6.37 (dd, J=7.4, 0.9, 1H).

Aufarbeitung

  1. temperaturecooled to rt
  2. extractionextracted with n-butanol (3×200 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified (FCC, 2 N NH3 in MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-545dbf0f64434acab0928dfc9354bc3c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877769B2

Verknüpfte Notizen

Wird geladen…