反応 #165516

反応方程式

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

収率 43.0%

溶媒

EtOAc

反応条件

後処理

1. 1
   洗浄sequentially washed with water (25 mL)
2. 2
   乾燥The organic layer was dried (Na2SO4)
3. 3
   濃縮concentrated under reduced pressure
4. 4
   その他The resulting solids were triturated with an EtOAc solution (80% EtOAc/20% hexane)

実験手順

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.

出典