Реакция #2012640

Уравнение реакции

N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]aminoquinolin-3-yl}-3-methoxypropionamide

ammonia

N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]quinolin-3-yl}-3-methoxypropionamide

ammonia

→

N-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide

Выход 167.2%

Растворители

methanol

methanol

Условия реакции

Обработка

1. 1
   ДругоеBoth vessels were sealed
2. 2
   ДругоеThe reaction mixtures
3. 3
   Другоеthe solvent was removed under reduced pressure
4. 4
   ДругоеThe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
5. 5
   ПромывкаThe organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine
6. 6
   Сушкаdried over sodium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated under reduced pressure

Методика

A Parr bomb was charged with 25.0 g of N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]aminoquinolin-3-yl}-3-methoxypropionamide and ammonia in methanol (300 mL of 7 N). A second vessel was charged with 30.21 g of N-{2-chloro-4-[2-(methanesulfonylamino)-2-methylpropyl]quinolin-3-yl}-3-methoxypropionamide and ammonia in methanol (400 mL of 7 N). Both vessels were sealed and then heated at 170° C. for 14 hours. The reaction mixtures were combined and the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure to provide 38.16 g of N-{2-[4-amino-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide as an off white foam.

Источник