반응 #9541

반응 방정식

tert-butyl 4-[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-oxidopiperazine-1-carboxylate

Phosphorous trichloride

→

7-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride

수율 84.2%

용매

chloroform

반응 조건

후처리

1. 1
   온도to warm to ambient temperature
2. 2
   기타The chloroform was removed under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethanol (150 mL)
4. 4
   workup.ADDITIONHydrogen chloride (21.5 mL of a 3 M solution in ethanol) was added
5. 5
   온도the reaction was heated
6. 6
   온도at reflux for 25 minutes
7. 7
   온도to cool to room temperature
8. 8
   기타a precipitate formed
9. 9
   기타was isolated by filtration

실험 절차

A solution of tert-butyl 4-[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-oxidopiperazine-1-carboxylate (8.84 g, 16.1 mmol) in chloroform (400 mL) was cooled to 4° C. Phosphorous trichloride (9.82 mL, 113 mmol) was added dropwise, and the reaction was stirred for 45 minutes at 4° C. Water (one drop) was added to the reaction, which was allowed to warm to ambient temperature. The chloroform was removed under reduced pressure, and the residue was dissolved in ethanol (150 mL). Hydrogen chloride (21.5 mL of a 3 M solution in ethanol) was added, and the reaction was heated at reflux for 25 minutes. The reaction was allowed to cool to room temperature; a precipitate formed and was isolated by filtration to provide 6.86 g of 7-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride as a light yellow solid.

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