Reaktion #60653

Reaktionsgleichung

charcoal

Methoxypropionyl chloride

triethylamine

tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate

triethylamine

→

tert-butyl 2-{2-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate

Ausbeute 90.8%

Lösungsmittel

EtOH

methanol

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was then concentrated under reduced pressure
2. 2
   Sonstigeto give an orange solid
3. 3
   TemperaturThe mixture was heated
4. 4
   Temperaturto reflux
5. 5
   workup.STIRRINGstirred under N2 overnight
6. 6
   EinengenThe reaction was then concentrated to dryness under reduced pressure
7. 7
   workup.ADDITIONtreated with 300 mL of Et2O
8. 8
   FiltrationThe mixture was then filtered
9. 9
   Einengenthe filtrate was concentrated under reduced pressure
10. 10
    Sonstigeto give a brown solid
11. 11
    FiltrationThe hot solution was filtered
12. 12
    Einengenconcentrated

Vorschrift

A solution of tert-butyl 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethylcarbamate (10.2 g, 29.5 mmol) in 250 mL of anhydrous CH2Cl2 was cooled to 0° C. and treated with triethylamine (4.18 mL, 30.0 mmol). Methoxypropionyl chloride (3.30 mL, 30.3 mmol) was then added dropwise over 5 min. The reaction was then warmed to room temperature and stirring was continued for 1 hour. The reaction mixture was then concentrated under reduced pressure to give an orange solid. This was dissolved in 250 mL of EtOH and 12.5 mL of triethylamine was added. The mixture was heated to reflux and stirred under N2 overnight. The reaction was then concentrated to dryness under reduced pressure and treated with 300 mL of Et2O. The mixture was then filtered and the filtrate was concentrated under reduced pressure to give a brown solid. The solid was dissolved in 200 mL of hot methanol and treated with activated charcoal. The hot solution was filtered and concentrated to give 11.1 g of tert-butyl 2-{2-[2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethoxy}ethylcarbamate as a yellow syrup.

Quelle