Reaction #44960

Reaction equation

t-butanol

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

triethylamine

diphenylphosphoryl azide

→

title compound

t-Butyl [2-{[(5-chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridin-5-yl]carbamate

Conditions

Workup

1. 1
   ConcentrationThe reaction solution is concentrated under reduced pressure
2. 2
   workup.ADDITIONThe residue is diluted with chloroform
3. 3
   Washwashed with water and saturated brine
4. 4
   DryingThe organic layer is dried over sodium sulfate
5. 5
   Otherthe solvent is evaporated under reduced pressure
6. 6
   OtherThe resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol=100/1 followed by 20/1)

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 (6.80 g) obtained in Example 79 is suspended in t-butanol (300 ml). To the suspension are added triethylamine (3.48 ml) and diphenylphosphoryl azide (5.39 ml) at room temperature, and the mixture is stirred at 100° C. for 15 hours. The reaction solution is concentrated under reduced pressure. The residue is diluted with chloroform, and washed with water and saturated brine. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol=100/1 followed by 20/1) to give the title compound (5.64 g).

Source