Indene oxide → Methyl 8-(trans-2,3-dihydro-2-hydroxy-1-indenylamino)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylate

HRID 2053033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053033
[NH2:1][C:2]1[C:3]2[N:4]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1.[O:17]1[CH:19]2[CH2:20][C:21]3[C:26]([CH:18]12)=[CH:25][CH:24]=[CH:23][CH:22]=3>O1CCOCC1.O>[OH:17][C@@H:19]1[CH2:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:18]1[NH:1][C:2]1[C:3]2[N:4]([C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=1

Komponenten

5

Edukt 2

HCID 92838Indene oxideHCID 9855934Methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate

Produkt 1

HCID 69114655Methyl 8-(trans-2,3-dihydro-2-hydroxy-1-indenylamino)-2,3-dimethyl-imidazo[1,2-a]pyridine-6-carboxylateAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

10.0 g (45.7 mmol) methyl 8-amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxylate and 18.1 g (137 mmol) 1,2-epoxyindane are suspended in 300 ml dioxane and 100 ml water. The reaction mixture is stirred at 100° C. for 2.5 d. After cooling down in an ice bath, the precipitate is collected and washed with water. The product is suspended in a mixture of 2-propanol and acetone (1:1) and filtered by suction. After drying in vacuo at 50° C., 12.4 g (77%) of the title compound are isolated as a colourless solid (m.p. 261-262° C.).

Aufarbeitung

  1. temperatureAfter cooling down in an ice bath
  2. customthe precipitate is collected
  3. washwashed with water
  4. additionThe product is suspended in a mixture of 2-propanol and acetone (1:1)
  5. filtrationfiltered by suction
  6. customAfter drying in vacuo at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-12d97191e9f343a88eea1df5e211cf0d
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326718B2

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