1,2-Dichloroethane → 5-isobutyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazol-2-amine

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (200 mg, 0.91 mmol) in methylene chloride (4.5 ml) was added 1,1′-thiocarbonyldipyridin-2(1H)-one (212 mg, 0.91 mmol) and stirred at room temperature for 1 hour. Upon complete formation of the isothiocyanate, 3-methylbutanehydrazide (159 mg, 1.37 mmol) was added to the mixture and stirred at room temperature for overnight. EDC (315 mg, 1.64 mmol) was then added and the reaction stirred at room temperature for 14 hours. The reaction was concentrated to dryness and taken up in water to form a slurry. The slurry was filtered and washed with water to afford the crude product, which was purified by column chromatography to afford the title compound as off-white solid after drying (217 mg, 69% yield). LC/MS, ESI-MS(+) m/z 344.1, RT 1.45 (Condition R).

1. stirringstirred at room temperature for overnight
2. stirringthe reaction stirred at room temperature for 14 hours
3. concentrationThe reaction was concentrated to dryness
4. customto form a slurry
5. filtrationThe slurry was filtered
6. washwashed with water
7. customto afford the crude product, which
8. customwas purified by column chromatography

ORD 기록

ord-ed005af77e91469691fd62a286bd34c3

출처 데이터셋

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08993619B2