Реакция #595307

Уравнение реакции

N—[[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]carbonyl]glycine

title product

N—[[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]carbonyl]glycine

trimethylacetyl chloride

2-methoxyethylamine

triethylamine

→

title compound

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-[(2-methoxyethyl)amino]-2-oxoethyl]-1-naphthalenecarboxamide

Растворители

dichloromethane

pyridine

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature overnight
2. 2
   Другоеquenched with water
3. 3
   Экстракцияextracted with dichloromethane
4. 4
   Промывкаwashed with brine
5. 5
   Сушкаdried with anhydrous sodium sulfate
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe residue was purified by column chromatography on silica gel

Методика

To a stirred solution of N—[[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]carbonyl]glycine (i.e. the title product of Step B) (100 mg) and pyridine (0.019 mL) in dichloromethane (3 mL) was added trimethylacetyl chloride (0.029 mL). The reaction mixture was stirred at room temperature for 2 h, and then 2-methoxyethylamine (0.11 mL) and triethylamine (0.68 mL, 5.0 mmol) were added. The reaction mixture was stirred at room temperature overnight, quenched with water, extracted with dichloromethane, washed with brine, dried with anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel using hexanes/ethyl acetate (3:2 to 1:4) as eluent to afford the title compound, a compound of the present invention, as a white solid (71 mg, 0.13 mmol, 65% yield).

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