반응 #634501

반응 방정식

2-(ethoxymethyl)-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine

hydrogen

sodium hydroxide

→

2-(ethoxymethyl)-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine

수율 75.8%

용매

trifluoroacetic acid

water

반응 조건

후처리

1. 1
   여과The mixture was filtered through CELITE
2. 2
   여과filter agent, which
3. 3
   세척was washed afterwards with dichloromethane
4. 4
   농축The filtrate was concentrated under reduced pressure
5. 5
   기타to afford an oil that
6. 6
   추출The mixture was extracted with dichloromethane (3×50 mL)
7. 7
   건조dried over sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated under reduced pressure
10. 10
    기타to yield a white solid
11. 11
    기타The solid was recrystallized from toluene

실험 절차

A mixture of 2-(ethoxymethyl)-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 9, 1.70 g, 4.04 mmol) and platinum(IV) oxide (1.0 g) in trifluoroacetic acid (20 mL) was hydrogenated on a Parr apparatus at 50 psi (3.5×105 Pa) hydrogen pressure for 40 hours. The mixture was filtered through CELITE filter agent, which was washed afterwards with dichloromethane. The filtrate was concentrated under reduced pressure to afford an oil that was suspended in water (20 mL) and adjusted to pH 13 with 50% aqueous sodium hydroxide. The mixture was extracted with dichloromethane (3×50 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield a white solid. The solid was recrystallized from toluene to afford 1.3 g of 2-(ethoxymethyl)-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a white, fluffy powder, mp 150-153° C.

출처