반응 #60653

반응 방정식

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

수율 90.8%

용매

EtOH

methanol

CH2Cl2

반응 조건

후처리

1. 1
   농축The reaction mixture was then concentrated under reduced pressure
2. 2
   기타to give an orange solid
3. 3
   온도The mixture was heated
4. 4
   온도to reflux
5. 5
   workup.STIRRINGstirred under N2 overnight
6. 6
   농축The reaction was then concentrated to dryness under reduced pressure
7. 7
   workup.ADDITIONtreated with 300 mL of Et2O
8. 8
   여과The mixture was then filtered
9. 9
   농축the filtrate was concentrated under reduced pressure
10. 10
    기타to give a brown solid
11. 11
    여과The hot solution was filtered
12. 12
    농축concentrated

실험 절차

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.

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