Potassium Iodide → 2,3-Dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427487
[NH2:1][C:2]1[C:3]2[N:4]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([C:8]([NH2:10])=[O:9])[CH:7]=1.[CH3:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:18]=1[CH2:19]Cl.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(Cl)Cl.CC(C)=O>[CH3:14][C:12]1[N:13]=[C:3]2[C:2]([NH:1][CH2:19][C:18]3[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:17]=3[CH3:16])=[CH:7][C:6]([C:8]([NH2:10])=[O:9])=[CH:5][N:4]2[C:11]=1[CH3:15]

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 98557898-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide

Produkt 1

HCID 97972452,3-Dimethyl-8-(2,6-dimethylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamideAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide (0.6 g, 2.9 mmol), 2,6-dimethylbenzylchloride (0.45 g, 2.9 mmol), sodium carbonate (1.0 g, 9.4 mmol) and potassium iodide (0.2 g, 1.3 mmol) were added to acetone (25 ml) and refluxed for 19 h. Methylene chloride was added and inorganic salts were filtered off. The solution was washed with a bicarbonate solution, the organic layer was separated, dried and the solvents were evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (100:5) as eluent and the product was washed with diethyl ether to give 0.78 g (82%) of the title compound.

Aufarbeitung

  1. temperaturerefluxed for 19 h
  2. filtrationinorganic salts were filtered off
  3. washThe solution was washed with a bicarbonate solution
  4. customthe organic layer was separated
  5. customdried
  6. customthe solvents were evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. washthe product was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-902502254b77418a9937de17c4e2f2b3
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313137B1

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