Triethylamine → N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-methylpropanamide

HRID 1064410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064410
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:20]2[C:19]([CH3:21])=[C:18]([CH3:22])[N:17]=[C:16]([NH2:23])[C:15]=2[N:14]=[C:13]1[CH3:24].[C:25](Cl)(=[O:29])[CH:26]([CH3:28])[CH3:27]>C(Cl)(Cl)Cl>[NH2:23][C:16]1[C:15]2[N:14]=[C:13]([CH3:24])[N:12]([CH2:11][CH2:10][CH2:9][NH:8][C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])[C:20]=2[C:19]([CH3:21])=[C:18]([CH3:22])[N:17]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 219460311-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Produkt 1

HCID 10236530N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-methylpropanamideAusbeute 25,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Triethylamine (0.78 mL, 5.6 mmol) was added to a solution of 1-(3-aminopropyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin4-amine (1.00 g, 4.3 mmol) in chloroform (50 mL). The solution was cooled in an ice bath and then isobutyryl chloride (0.49 mL, 4.7 mmol) was added. The reaction mixture was stirred for 15 minutes then the ice bath was removed and the reaction mixture was stirred for an additional 15 minutes. The reaction mixture was diluted with chloroform to a volume of 150 mL. Water (50 mL) was added then the pH was adjusted to 11 with solid potassium carbonate and then to pH 14 with 50% sodium hydroxide. The resulting precipitate was isolated by filtration and dried to provide 0.33 g of N-[3-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)propyl]-2-methylpropanamide as a white solid, m.p. 178.1-178.8° C.

Aufarbeitung

  1. temperatureThe solution was cooled in an ice bath
  2. customthe ice bath was removed
  3. stirringthe reaction mixture was stirred for an additional 15 minutes
  4. additionThe reaction mixture was diluted with chloroform to a volume of 150 mL
  5. additionWater (50 mL) was added
  6. customThe resulting precipitate was isolated by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-71262cf3df9249c0b4348f388b7474b4
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969722B2

Notizen zur Reaktion

Wird geladen…