Chloroacetaldehyde → Methyl 3-imidazo[1,2-b]pyridazin-7-ylbenzoate

HRID 407076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 407076
[NH2:1][C:2]1[N:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:3]=1.Cl[CH2:19][CH:20]=O>O.C(O)(C)C>[N:1]1[CH:19]=[CH:20][N:7]2[C:2]=1[CH:3]=[C:4]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[N:6]2

Komponenten

5

Edukt 2

HCID 33ChloroacetaldehydeHCID 67980189Methyl 3-(6-aminopyridazin-4-yl)benzoate

Produkt 1

HCID 67980108Methyl 3-imidazo[1,2-b]pyridazin-7-ylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of methyl 3-(6-aminopyridazin-4-yl)benzoate (0.20 g, 0.87 mmol) and chloroacetaldehyde in water (0.3 mL, 50%) in isopropyl alcohol (3.0 mL) was stirred at 100° C. for 4 h. The solvent was removed and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-30%) to afford the desired product (0.18 g). LCMS (M+H)+: m/z=254.1

Aufarbeitung

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-30%)

Quellen und Nachweise

ORD-Eintrag
ord-0232e37fabdc4918b0b3d55ffea65bb1
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754114B2

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