Реакция #438366

Уравнение реакции

N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

N-methylmorpholine

picolinic acid

1-hydroxybenzotriazole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

→

amide

Выход 131.1%

N-[[4-[[(2-pyridinylmethyl)amino]methyl]phenyl]methyl]-N-(5,6,7,8-tetrahydro-8-quinolinyl)-picolinamide

Выход 131.1%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated
2. 2
   workup.ADDITIONThe residue was diluted with ethylacetate (300 mL)
3. 3
   Промывкаwashed with saturated aqueous NaHCO3
4. 4
   Сушкаbrine, dried (Na2SO4)
5. 5
   Другоеevaporated
6. 6
   ДругоеPurification of the crude material by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2)

Методика

To a stirred solution of N-(2-nitrobenzenesulfonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (209 mg, 0.39 mmol) in dry DMF (1 mL) was added N-methylmorpholine (0.5 mL, 4.45 mmol), picolinic acid (64 mg, 0.52 mmol), 1-hydroxybenzotriazole (57 mg, 0.42 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (85 mg, 0.44 mmol). The reaction mixture was allowed to stir at room temperature for further 18 hours and then concentrated. The residue was diluted with ethylacetate (300 mL) and washed with saturated aqueous NaHCO3, then brine, dried (Na2SO4) and evaporated. Purification of the crude material by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2) gave the desired amide (237 mg, 94%) as a yellow oil.

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