Reacción #44963

Ecuación de reacción

sodium hydrogen carbonate

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

lithium borohydride

hydrochloric acid

→

title compound

Rendimiento 28.1%

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

Rendimiento 28.1%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Temperaturacooling
3. 3
   workup.STIRRINGthe mixture is stirred at room temperature for 15 minutes
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe organic layer is washed with saturated brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Otrothe solvent is evaporated under reduced pressure
8. 8
   OtroThe resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=10/1)
9. 9
   Filtracióncollected by filtration

Procedimiento

Methyl 2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-5-carboxylate (300 mg) obtained in Example 39 is suspended in tetrahydrofuran (15 ml), and thereto is added lithium borohydride (24 mg) under ice-cooling, and the mixture is stirred at room temperature for 20 hours. To the reaction solution is poured 10% hydrochloric acid under ice-cooling, and the mixture is stirred at room temperature for 15 minutes. The reaction solution is alkalified with saturated aqueous sodium hydrogen carbonate solution, and then extracted with ethyl acetate. The organic layer is washed with saturated brine and dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: ethyl acetate followed by ethyl acetate/methanol=10/1). The resulting solid is suspended in diethyl ether-n-hexane and collected by filtration to give the title compound (80 mg).

Fuente