Dimethylacetamide → Ammonium Hydroxide

HRID 981060

Reaktionsgleichung

Reaktionsgleichung von HRID 981060
[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:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]Cl)=CN=2)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]1.C[C:32]([N:34](C)C)=O>>[NH4+:1].[OH-:17].[CH:26]1([N:15]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[C:16]([C:18]2[CH:32]=[N:34][C:21]([CH2:24][N:9]3[CH:8]=[CH:7][C:6]4=[N:3][CH:2]=[N:1][C:5]4=[CH:4]3)=[CH:22][CH:23]=2)=[O:17])[CH2:27][CH2:28][CH2:29][CH2:30]1

Komponenten

5

Edukt 3

HCID 31374DimethylacetamideHCID 67504Imidazo(4,5-b)pyridineHCID 20071627N,N-dicyclopentyl-5-(chloromethyl)-2-pyridinecarboxamide

Produkt 2

HCID 14923Ammonium HydroxideHCID 20071631N,N-dicyclopentyl-6-(5H-imidazo[4,5-c]pyridin-5-yl-methyl)-3-pyridinecarboxamide

Versuchsvorschrift

To a stirred solution of imidazopyridine in dimethylacetamide under argon, N,N-dicyclopentyl-5-(chloromethyl)-2-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 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 dry ether
  4. filtrationfiltered
  5. customThe crude product is chromatographed on silica gel using mixtures of CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-f4c7ff7eb9fd4c1581dfe127113601ae
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990518

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