تفاعل #165516

معادلة التفاعل

H2O

N-methylmorpholine

EDCI.HCl

DMF

4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-aminophenyl)urea

mono-methyl isophthalate

HOBT

→

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

المردود 43.0%

المذيبات

EtOAc

ظروف التفاعل

المعالجة

1. 1
   غسيلsequentially washed with water (25 mL)
2. 2
   تجفيفThe organic layer was dried (Na2SO4)
3. 3
   تركيزconcentrated under reduced pressure
4. 4
   أخرىThe resulting solids were triturated with an EtOAc solution (80% EtOAc/20% hexane)

الإجراء التجريبي

To a solution of N-(4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-aminophenyl)urea (Method C1d; 0.050 g, 1.52 mmol), mono-methyl isophthalate (0.25 g, 1.38 mmol), HOBT.H2O (0.41 g, 3.03 mmol) and N-methylmorpholine (0.33 mL, 3.03 mmol) in DMF (8 mL) was added EDCI.HCl (0.29 g, 1.52 mmol). The resulting mixture was stirred at room temp. overnight, diluted with EtOAc (25 mL) and sequentially washed with water (25 mL) and a saturated NaHCO3 solution (25 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The resulting solids were triturated with an EtOAc solution (80% EtOAc/20% hexane) to give N-(4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-(3-methoxycarbonylphenyl)carboxyaminophenyl)urea (0.27 g, 43%): mp 121-122; TLC (80% EtOAc/20% hexane) Rf 0.75.

المصدر