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Sodium Iodide → 2-Methyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427493
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 427493
[NH2:1][C:2]1[C:3]2[N:4]([CH:11]=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([C:8]([NH2:10])=[O:9])[CH:7]=1.[CH2:15]([C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:18]=1[CH2:19]Cl)[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)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[CH2:15][CH3:16])=[CH:7][C:6]([C:8]([NH2:10])=[O:9])=[CH:5][N:4]2[CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 121489182-Ethyl-6-methylbenzyl chlorideHCID 183574418-Amino-2-methylimidazo[1,2-a]pyridine-6-carboxamide

Produkt 1

HCID 99271772-Methyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamideAusbeute 2,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

8-Amino-2-methylimidazo[1,2-a]pyridine-6-carboxamide (3.8 g, 20 mmol), 2-ethyl-6-methylbenzylchloride (2.8 g, 17 mmol), potassium carbonate (5.5 g, 40 mmol) and sodium iodide (0.1 g, 0.6 mmol) were added to dimethylformamide (75 ml) and the mixture was stirred at 50° C. for 4 h. and at room temperature for 48 h. The reaction mixture was filtred through silica gel and the gel was washed with methylene chloride. The solvents were evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent. Crystallization from a mixture of methylene chloride and hexane gave 0.13 g (2%) of the title compound.

Aufarbeitung

  1. washthe gel was washed with methylene chloride
  2. customThe solvents were evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel
  4. customCrystallization
  5. additionfrom a mixture of methylene chloride and hexane

Quellen und Nachweise

ORD-Eintrag
ord-6e113a46d2d6435da55d950a7f14f2a5
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06313137B1

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