Реакция #73050

Уравнение реакции

butyryl chloride

triethylamine

butyryl chloride

4-{[(3-amino-2-chloroquinolin-4-yl)amino]methyl}tetrahydro-2H-thiopyran-4-ol

triethylamine

→

N-(2-chloro-4-{[(4-hydroxytetrahydro-2H thiopyran-4-yl)methyl]amino}quinolin-3-yl)butanamide

Растворители

sodium bicarbonate

dichloromethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture was stirred for an additional hour
2. 2
   Экстракцияextracted with dichloromethane (3×60 mL)
3. 3
   ПромывкаThe combined organics were washed with saturated aqueous sodium bicarbonate (40 mL) and brine (30 mL)
4. 4
   Сушкаdried over sodium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under reduced pressure

Методика

Under a nitrogen atmosphere butyryl chloride (322 μL, 3.11 mmol) was added dropwise was added to a suspension of 4-{[(3-amino-2-chloroquinolin-4-yl)amino]methyl}tetrahydro-2H-thiopyran-4-ol (0.92 g, 2.83 mmol) in dichloromethane (28 mL). After 2 hours triethylamine (0.79 mL, 5.66 mol) was added and the reaction mixture was stirred for 2 hours. More butyryl chloride (0.2 mL) and triethylamine (0.30 mL) were added. The reaction mixture was stirred for an additional hour and then diluted with saturated aqueous sodium bicarbonate (50 mL) and extracted with dichloromethane (3×60 mL). The combined organics were washed with saturated aqueous sodium bicarbonate (40 mL) and brine (30 mL), dried over sodium sulfate, filtered, and then concentrated under reduced pressure to provide N-(2-chloro-4-{[(4-hydroxytetrahydro-2H thiopyran-4-yl)methyl]amino}quinolin-3-yl)butanamide as an off-white solid.

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