Реакция #2358535

Уравнение реакции

triethylamine

3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid

EDCI

→

N-cyclopropyl-3-(5-dimethylcarbamoyl-pent-1-ynyl)benzamide

Выход 91.0%

N-Cyclopropyl-3-(5-dimethylcarbamoyl-pent-1-ynyl)benzamide

Выход 91.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONCyclopropyilamine (0.027 g, 0.38 mmol) was then added
2. 2
   workup.STIRRINGthe mixture stirred at room temperature for 16 hrs
3. 3
   ПромывкаThe reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL)
4. 4
   ДругоеThe organic layer was separated
5. 5
   Сушкаdried over magnesium sulfate
6. 6
   Другоеthe solvent evaporated under vacuum
7. 7
   ДругоеThe residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient)

Методика

To a solution of 3-(5-dimethylcarbamoyl-pent-1-ynyl)-benzoic acid (0.100 g, 0.38 mmol) in dry dichloromethane (1.5 mL) under a nitrogen atmosphere at room temperature, EDCI (0.0728 g, 0.38 mmol) was added followed by triethylamine (0.162 mL, 1.14 mmol), the resulting mixture was stirred at room temperature for further minutes. Cyclopropyilamine (0.027 g, 0.38 mmol) was then added and the mixture stirred at room temperature for 16 hrs. The reaction mixture was washed with a mixture of saturated brine and saturated sodium bicarbonate (1:1; 2×150 mL) followed by saturated brine solution (100 mL). The organic layer was separated and dried over magnesium sulfate and the solvent evaporated under vacuum. The residue was purified by flash column chromatography on silica gel (DCM:MeOH, 95% to 5% methanol gradient) to afford N-cyclopropyl-3-(5-dimethylcarbamoyl-pent-1-ynyl)benzamide (25) (0.10 g, 0.34 mmol, 91% yield).

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