Реакция #9481

Уравнение реакции

pyridine-3-boronic acid 1,3-propanediol cyclic ester

methoxypropanoyl chloride

7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

→

7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

2-(2-methoxyethyl)-1-(2-methylpropyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was heated
2. 2
   Температураat reflux overnight
3. 3
   ДругоеThe crude product was purified by flash column chromatography on silica gel (
4. 4
   Промывкаeluting with chloroform
5. 5
   ДругоеCMA in a gradient from 90:10 to 76:24) followed by recrystallization from methanol
6. 6
   ДругоеThe crystals were dried at 1.33 Pa and 98° C.

Методика

7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine was prepared according to the procedures described in Parts A and B of Example 9 using methoxypropanoyl chloride instead of ethoxyacetyl chloride. 7-Bromo-2-(2-methoxyethyl)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine was coupled with pyridine-3-boronic acid 1,3-propanediol cyclic ester according to the method described in Examples 118–121. The reaction was heated at reflux overnight, and the work-up procedure described in Part F of Examples 125–131 was followed. The crude product was purified by flash column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 90:10 to 76:24) followed by recrystallization from methanol. The crystals were dried at 1.33 Pa and 98° C. to provide 2-(2-methoxyethyl)-1-(2-methylpropyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine as white needles, mp 207–208° C.

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