Benzoyl chloride → N-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]benzamide

HRID 1060662

Reaktionsgleichung

Reaktionsgleichung von HRID 1060662
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21]2[C:20]([CH3:22])=[C:19]([CH3:23])[N:18]=[C:17]([NH2:24])[C:16]=2[N:15]=[C:14]1[CH2:25][CH2:26][CH2:27][CH3:28].[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(S(O)(=O)=O)C>ClCCl.C(O)(C)C>[NH2:24][C:17]1[C:16]2[N:15]=[C:14]([CH2:25][CH2:26][CH2:27][CH3:28])[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:21]=2[C:20]([CH3:22])=[C:19]([CH3:23])[N:18]=1

Komponenten

7

Edukt 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11668Ethanesulfonic acidHCID 120210831-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Produkt 1

HCID 10216053N-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]benzamideAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (0.07 mL, 0.5 mmol) was added to a solution of 1-(4-aminobutyl)-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (150 mg, 0.5 mmol) in dichloromethane (150 mL). The reaction mixture was cooled in an ice bath. Benzoyl chloride (0.07 mL, 0.5 mmol) was added and the reaction mixture was removed from the ice bath. The reaction mixture was washed twice with water and then concentrated under reduced pressure. The resulting residue was purified by flash chromatography eluting with 10% methanol in dichloromethane to provide an oily brown material. This material was dissolved in a minimum amount of isopropanol and then ethanesulfonic acid (55 mg, 0.5 mmol) was added with stirring. The reaction mixture was stirred at ambient temperature for ˜1 hour and then heated briefly in a sand bath until it became homogeneous. The solution was allowed to cool to ambient temperature and then was chilled in an ice bath. The resulting precipitate was isolated by filtration to provide 111 mg of N-[4-(4-amino-2-butyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]benzamide as a crystalline solid, m.p. 127.8-128.8° C. Analysis: Calculated for C23H31N5O: % C, 70.20; % H, 7.94; % N, 17.80; Found: % C, 69.82; % H, 7.70; % N, 17.68.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customthe reaction mixture was removed from the ice bath
  3. washThe reaction mixture was washed twice with water
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by flash chromatography
  6. washeluting with 10% methanol in dichloromethane
  7. customto provide an oily brown material
  8. stirringThe reaction mixture was stirred at ambient temperature for ˜1 hour
  9. temperatureheated briefly in a sand bath until it
  10. temperaturewas chilled in an ice bath
  11. customThe resulting precipitate was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-c7c9995ba1fe4274a2bf60052de5dfac
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525064B1

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