反応 #8888

反応方程式

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

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
2. 2
   洗浄The organic layer was washed twice with saturated NaHCO3 solution, brine
3. 3
   乾燥dried (Na2SO4)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他Purification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient)

実験手順

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.

出典