Reacción #2302712

Ecuación de reacción

Phenyl N-(4-(1-(methylamino)carbonyl-1H-indol-5-yloxy)-pyridin-2-yl)-N-(phenoxycarbonyl)carbamate

sodium hydroxide

1,1-dioxothiomorpholine hydrochloride

→

title compound

Rendimiento 81.3%

N1-Methyl-5-(2-((1,1-dioxothiomorpholin-4-ylcarbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide

Rendimiento 81.3%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was partitioned between ethyl acetate and water
2. 2
   SecadoThe organic layer was dried over anhydrous magnesium sulfate
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   OtroThe residue was purified by silica gel column chromatography (Fuji Silysia BW-300, ethyl acetate)
5. 5
   workup.ADDITIONDiethyl ether was added to
6. 6
   Otroto crystallize
7. 7
   Filtraciónand the crystals were filtered off
8. 8
   Lavadowashed with diethyl ether
9. 9
   Otrodried under aeration

Procedimiento

Phenyl N-(4-(1-(methylamino)carbonyl-1H-indol-5-yloxy)-pyridin-2-yl)-N-(phenoxycarbonyl)carbamate (150 mg, 0.278 mmol, Production example 5-2) was dissolved in N,N-dimethylformamide (1.5 ml); 5N aqueous solution of sodium hydroxide (0.29 ml) and 1,1-dioxothiomorpholine hydrochloride (246 mg, 1.44 mmol) were added thereto; and the reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia BW-300, ethyl acetate). Diethyl ether was added to this to allow to crystallize; and the crystals were filtered off, washed with diethyl ether, and dried under aeration to yield the title compound as colorless crystals (100 mg, 0.226 mmol, 78.5%).

Fuente