Acetic Acid → HCID 882263, compound

To 2-p-tolylbenzo[d]oxazol-5-amine (500 mg, 2.32 mmol) in 1,2-dichloroethane (20 mL) at room temperature was added acetic acid (142 μL, 2.32 mmol) and isonicotinaldehyde (222.5 μL, 2.29 mmol) and the mixture was stirred for 1 h. Sodium triacetoxyborohydride (707 mg, 3.35 mmol) was then added and the mixture was stirred at room temperature for 24 h. The mixture was then diluted with dichloromethane and the organic layer was washed with saturated aqueous NaHCO3. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate:hexanes 20:80 to afford 328 mg (47%) of the title compound (LCMS RT=6.27 min, MH+ 316.1)

1. stirringthe mixture was stirred at room temperature for 24 h
2. washthe organic layer was washed with saturated aqueous NaHCO3
3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
4. customevaporated
5. customThe resulting solid was purified by column chromatography
6. washeluting with ethyl acetate:hexanes 20:80

ORD record

ord-f871c23f58694d7fa7ad2f5f06607800

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518980B2