Imidazo(4,5-b)pyridine → N,N-dicyclopentyl-6-[3-(5H-imidazo[4,5-c]pyridin-5-yl)propyl]-3-pyridinecarboxamide

HRID 981058

Reaktionsgleichung

Reaktionsgleichung von HRID 981058
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[N:3]=[CH:2]1.[CH:10]1([N:15]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:16]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26]Cl)=[N:22][CH:23]=2)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]1>CC(N(C)C)=O>[CH3:16][OH:17].[NH4+:1].[OH-:17].[CH:28]1([N:15]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[C:16]([C:18]2[CH:23]=[N:22][C:21]([CH2:24][CH2:25][CH2:26][N:9]3[CH:8]=[CH:7][C:6]4=[N:3][CH:2]=[N:1][C:5]4=[CH:4]3)=[CH:20][CH:19]=2)=[O:17])[CH2:32][CH2:31][CH2:30][CH2:29]1

Komponenten

5

Edukt 2

HCID 67504Imidazo(4,5-b)pyridineHCID 20071636HCID 20071636, Verbindung

Produkt 2

HCID 20071638N,N-dicyclopentyl-6-[3-(5H-imidazo[4,5-c]pyridin-5-yl)propyl]-3-pyridinecarboxamideHCID 21894508Ammonium hydroxide methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a stirred solution of imidazopyridine in dimethylacetamide under argon, N,N-dicyclopentyl-2-(3-chloropropyl)-5-pyridinecarboxamide is added in one portion. The reaction temperature is slowly raised to 80°-85° C. and stirred for 24-60 hr. The reaction flask is cooled to room temperature and the solvent is removed under reduced pressure at <45° C. The residue is triturated with excess of dry ether and filtered The crude product is chromatographed on silica gel using mixtures of CH2Cl2 :MeOH NH4OH to give the title compound.

Aufarbeitung

  1. temperatureThe reaction temperature is slowly raised to 80°-85° C.
  2. customthe solvent is removed under reduced pressure at <45° C
  3. customThe residue is triturated with excess of dry ether
  4. filtrationfiltered The crude product
  5. customis chromatographed on silica gel using mixtures of CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-8ff414fc430d4cbea77029b51377d9c3
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990518

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