Reaktion #155864

Reaktionsgleichung

bis(trichloromethyl)carbonate

3-(methylthio)-1-phenyl-1H-indazol-6-amine

DIEA

tert-butyl 3-aminopyrrolidine-1-carboxylate

→

tert-butyl 3-(3-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)ureido)pyrrolidine-1-carboxylate

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 50-mL 3-necked round-bottom flask, was placed
2. 2
   workup.ADDITIONTo the resulting mixture was then added
3. 3
   workup.STIRRINGThe resulting solution was stirred for 3 h at 15° C
4. 4
   workup.STIRRINGwith stirring at 15° C. in 15 min
5. 5
   workup.STIRRINGThe resulting solution stirred for an additional 4 h at 15° C
6. 6
   EinengenThe resulting mixture was concentrated under vacuum

Vorschrift

Into a 50-mL 3-necked round-bottom flask, was placed a solution of bis(trichloromethyl)carbonate (200 mg, 0.67 mmol) in dichloromethane (3 mL). To the resulting mixture was then added a mixture of 3-(methylthio)-1-phenyl-1H-indazol-6-amine (500 mg, 1.96 mmol, 1.00 equiv) and DIEA (560 mg, 4.33 mmol, 2.21 equiv) in dichloromethane (2 mL) dropwise with stirring at 0° C. in 30 min. The resulting solution was stirred for 3 h at 15° C. The resulting mixture was added to a solution of tert-butyl 3-aminopyrrolidine-1-carboxylate (440 mg, 2.37 mmol, 1.21 equiv) in dichloromethane (3 mL) dropwise with stirring at 15° C. in 15 min. The resulting solution stirred for an additional 4 h at 15° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate:petroleum ether (1:4˜1:3) to yield tert-butyl 3-(3-(3-(methylthio)-1-phenyl-1H-indazol-6-yl)ureido)pyrrolidine-1-carboxylate as a white solid. MS: 468 (MH+).

Quelle