Reaktion #11442

Reaktionsgleichung

N-[4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide

ammonium acetate

hydrochloric acid

→

N-[4-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide

Ausbeute 59.1%

Lösungsmittel

chloroform

diethyl ether

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool
2. 2
   ExtraktionThe solution was extracted with 10% aqueous sodium hydroxide solution
3. 3
   SonstigeThe aqueous layer was separated
4. 4
   Extraktionextracted multiple times with chloroform
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Sonstigeto provide a yellow oil
8. 8
   SonstigeThe resulting white precipitate was isolated by filtration
9. 9
   Sonstigedried
10. 10
    workup.DISSOLUTIONThe solid was dissolved in water
11. 11
    SonstigeThe resulting white precipitate was isolated by filtration
12. 12
    Waschenwashed with diethyl ether
13. 13
    Sonstigedried in a vacuum oven at 80° C.

Vorschrift

N-[4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide (4.20 g, 10.4 mmol) and ammonium acetate (42 g) were combined and then heated in a sealed tube at 150° C. for 36 hrs. The reaction mixture was allowed to cool and then it was dissolved in chloroform. The solution was extracted with 10% aqueous sodium hydroxide solution. The aqueous layer was separated and then extracted multiple times with chloroform. The organic layers were combined, dried over magnesium sulfate and then concentrated under reduced pressure to provide a yellow oil. The oil was dissolved in methanol and combined with 1M hydrochloric acid in diethyl ether (10.4 mL). The resulting white precipitate was isolated by filtration and dried. The solid was dissolved in water and the solution was adjusted to pH 10 with solid sodium carbonate. The resulting white precipitate was isolated by filtration, washed with diethyl ether and then dried in a vacuum oven at 80° C. to provide 2.00 g of N-[4-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide, m.p. 228–230° C.

Quelle