Реакция #8888

Уравнение реакции

product

3-(Acetylamino)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo-[2,3-b]pyridine-2-carboxylic acid

2-azabicyclo[2.2.2]octane hydrochloride

EDC

1-methylmorpholine

→

title compound

N-[2-(2-Azabicyclo[2.2.2]oct-2-ylcarbonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-3-yl]acetamide

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
2. 2
   ПромывкаThe organic layer was washed twice with saturated NaHCO3 solution, brine
3. 3
   Сушкаdried (Na2SO4)
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеPurification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient)

Методика

A solution of 0.027 g (0.0568 mmol) of the product from Step A in CH2Cl2 (0.6 mL) was treated with 2-azabicyclo[2.2.2]octane hydrochloride (0.009 g; 0.0625 mmol), EDC (0.016 g; 0.0852 mmol), DMAP (0.007 g; 0.0568 mmol), and 1-methylmorpholine (19 μL; 0.170 mmol), then stirred at room temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 568.0 (M+1), 570.0 (M+3); Rt=4.68 min.

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