Reaction #44959

Reaction equation

2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-5-carboxylic acid

morpholine

1-hydroxybenzotriazole

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

title compound

N-(5-Chloropyridin-2-yl)-5-(morpholin-4-ylcarbonyl)-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-2-carboxamide

Solvents

ethyl acetate tetrahydrofuran

N,N-dimethylformamide

Conditions

Workup

1. 1
   Washthe solution is washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
2. 2
   Dryingdried over sodium sulfate
3. 3
   OtherThe solvent is evaporated under reduced pressure
4. 4
   OtherThe solid precipitates
5. 5
   Filtrationare collected by filtration

Procedure

2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-5-carboxylic acid (100 mg) obtained in Example 79 is dissolved in N,N-dimethylformamide (3 ml), and thereto are added successively morpholine (32 μl), 1-hydroxybenzotriazole (50 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (71 mg), and the mixture is stirred at room temperature for 15 hours. The reaction solution is diluted with ethyl acetate-tetrahydrofuran, and the solution is washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over sodium sulfate. The solvent is evaporated under reduced pressure and the resulting residue is suspended in ethyl acetate-diethyl ether. The solid precipitates are collected by filtration to give the title compound (109 mg).

Source