Triethylamine → 4-(methylamino)-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

HRID 339564

Reaktionsgleichung

Reaktionsgleichung von HRID 339564
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.ON1C2C=CC=CC=2N=N1.[CH3:28][NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:28][NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]4[CH:8]=3)=[CH:12][CH:13]=2)=[O:35])=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 663454-(Methylamino)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 8210844-(6-Methylimidazo[1,2-a]pyridin-2-yl)aniline

Produkt 1

HCID 583420774-(methylamino)-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamideAusbeute 33,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-(6-methylimidazo[1,2-a]pyridin-2-yl)aniline (0.10 g, 0.448 mmol), 1-hydroxybenzotriazole (0.06 g, 0.448 mmol), 4-methylaminobenzoic acid (0.068 g, 0.448 mmol) and triethylamine (62 μl, 0.045 g, 0.448 mmol) in dry DMF (5 ml) at 0° C. was added 1-ethyl-3-[3-(dimethylaminopropyl]-carbodiimide hydrochloride (0.086 g, 0.448 mmol) under an atmosphere or argon. After 10 min the cooling bath was removed and the reaction mixture was stirred at room temperature for 4 d. The reaction mixture was then added to water (150 ml) with stirring and the precipitate was collected by filtration. Purification by flash chromatography (25:1 DCM/MeOH) gave the title compound (0.053 g, 33%) as an almost colourless solid.

Aufarbeitung

  1. customAfter 10 min the cooling bath was removed
  2. additionThe reaction mixture was then added to water (150 ml)
  3. stirringwith stirring
  4. filtrationthe precipitate was collected by filtration
  5. customPurification by flash chromatography (25:1 DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-7e9a0e0620404989977747eea8dccf69
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

Verknüpfte Notizen

Wird geladen…