반응 #2302712

반응 방정식

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

sodium hydroxide

1,1-dioxothiomorpholine hydrochloride

→

title compound

수율 81.3%

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

수율 81.3%

용매

N,N-dimethylformamide

반응 조건

후처리

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

실험 절차

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%).

출처