Reaktion #2325482

Reaktionsgleichung

4-tert-butyl-N-(4-chloro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide

5-methyl-oxazole-4-carboxylic acid methylamide

pyridine

→

title compound

4-tert-Butyl-N-{4-chloro-2-[4-methyl-5-(5-methyl-oxazol-4-yl)-4H-[1,2,4]triazol-3-yl]-phenyl}-benzenesulfonamide

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was subsequently warmed to −10° C. over 2.5 h
2. 2
   TemperaturThe reaction was warmed to room temperature
3. 3
   EinengenThe solvent was concentrated in vacuo and ethanol (5 mL) and diisopropylamine (0.5 mL)
4. 4
   workup.ADDITIONwere added
5. 5
   workup.STIRRINGthe solution stirred at 90° C. overnight
6. 6
   EinengenThe following day, the reaction was concentrated in vacuo
7. 7
   Sonstigethe crude material was purified by flash column chromatography (10-100% ethyl acetate and hexane)

Vorschrift

A vial was charged with 5-methyl-oxazole-4-carboxylic acid methylamide (71 mg, 0.5 mmol), pyridine (0.12 mL, 1.5 mmol), and anhydrous dichloromethane (2.5 mL). The reaction vessel was cooled to −40° C. and trifluoromethanesulfonyl anhydride (0.11 mL, 0.65 mmol) was added. The reaction was subsequently warmed to −10° C. over 2.5 h and then 4-tert-butyl-N-(4-chloro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide (191 mg, 0.5 mmol) was added. The reaction was warmed to room temperature stirred an additional 2 h. The solvent was concentrated in vacuo and ethanol (5 mL) and diisopropylamine (0.5 mL) were added and the solution stirred at 90° C. overnight. The following day, the reaction was concentrated in vacuo and the crude material was purified by flash column chromatography (10-100% ethyl acetate and hexane), followed by preparative HPLC (10-90% gradient of MeCN-water) to yield the title compound: MS (ES) M+H expected 486.1, found 486.0.

Quelle