Реакция #73077

Уравнение реакции

hydrazine

2-({4-amino-1-[(1-hydroxycyclobutyl)methyl]-1H-imidazo[4,5-c]quinolin-2-yl}methyl)-1H-isoindole-1,3(2H)-dione

→

1-{[4-amino-2-(aminomethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclobutanol

Выход 59.1%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ДругоеThe ethanol was removed under reduced pressure
2. 2
   Другоеthe resulting white solid was triturated with 2 N hydrochloric acid
3. 3
   ФильтрацияThe resulting suspension was filtered
4. 4
   Другоеto remove a solid
5. 5
   Промывкаthe filter cake was washed with water
6. 6
   workup.ADDITIONThe filtrate was made basic with the addition of solid sodium bicarbonate
7. 7
   ДругоеA precipitate formed
8. 8
   Другоеwas isolated by filtration
9. 9
   Промывкаwashed with water
10. 10
    Другоеdried at 50° C. for three days in a vacuum oven

Методика

Under a nitrogen atmosphere, hydrazine (0.89 mL, 28 mmol) was added to a suspension of 2-({4-amino-1-[(1-hydroxycyclobutyl)methyl]-1H-imidazo[4,5-c]quinolin-2-yl}methyl)-1H-isoindole-1,3(2H)-dione (2.42 g, 5.66 mmol) in ethanol (57 mL), and the reaction was stirred for two hours at room temperature. The ethanol was removed under reduced pressure, and the resulting white solid was triturated with 2 N hydrochloric acid. The resulting suspension was filtered to remove a solid, and the filter cake was washed with water. The filtrate was made basic with the addition of solid sodium bicarbonate. A precipitate formed and was isolated by filtration, washed with water, and dried at 50° C. for three days in a vacuum oven to provide 0.994 g of 1-{[4-amino-2-(aminomethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclobutanol as a yellow solid.

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