تفاعل #73050

معادلة التفاعل

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

المذيبات

sodium bicarbonate

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر