Реакция #165517

Уравнение реакции

4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-(3-methylcarbamoylphenyl) carboxyaminophenyl)urea

3-methylcarbamoylaniline

N-methylmorpholine

EDCI.HCl

HOBT

→

4-chloro-3-((trifluoro methyl)phenyl)-N′-(4-(3-methylcarbamoylphenyl)carbamoylphenyl)urea

Выход 41.0%

Растворители

water

DMF

H2O

Условия реакции

Обработка

1. 1
   Температураto warm to room temp.
2. 2
   Экстракцияextracted with EtOAc (25 mL)
3. 3
   КонцентрированиеThe organic phase was concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe resulting yellow solids were dissolved in EtOAc (3 mL)
5. 5
   Фильтрацияthen filtered through a pad of silica gel (17 g, gradient from 70% EtOAc/30% hexane to 10% MeOH/90% EtOAc)

Методика

To a solution of N-(4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-(3-methylcarbamoylphenyl) carboxyaminophenyl)urea (0.14 g, 0.48 mmol), 3-methylcarbamoylaniline (0.080 g, 0.53 mmol), HOBT.H2O (0.14 g, 1.07 mmol), and N-methylmorpholine (0.5 mL, 1.07 mmol) in DMF (3 mL) at 0° C. was added EDCI.HCl (0.10 g, 0.53 mmol). The resulting mixture was allowed to warm to room temp. and was stirred overnight. The resulting mixture was treated with water (10 mL), and extracted with EtOAc (25 mL). The organic phase was concentrated under reduced pressure. The resulting yellow solids were dissolved in EtOAc (3 mL) then filtered through a pad of silica gel (17 g, gradient from 70% EtOAc/30% hexane to 10% MeOH/90% EtOAc) to give N-(4-chloro-3-((trifluoro methyl)phenyl)-N′-(4-(3-methylcarbamoylphenyl)carbamoylphenyl)urea as a white solid (0.097 g, 41%): mp 225-229; TLC (100% EtOAc) Rf 0.23.

Источник