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

Temperature

-40 °C

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.

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

ORD record

ord-b618ed4e913845c9848c2cdcf963da1e

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07718683B2