1-Hydroxybenzotriazole → HCID 178456943, compound

2,4-Bis(trifluoromethyl)benzoic acid (1.20 g) was added to a solution of 1-hydroxybenzotriazole (0.76 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.07 g), (5Z)-4-(methylamino)-5-(piperidin-4-ylmethylidene)-1,3-thiazol-2(5H)-one dihydrochloride (1.5 g), triethylamine (1.3 mL) in DMF (50 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (1.7 g).

1. extractionthe mixture was extracted with ethyl acetate
2. washThe extract was washed with water and saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customthe solvent was evaporated under reduced pressure
5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
6. customrecrystallized from ethyl acetate/heptane

ORD record

ord-42eee78d5a0540d49c6424370d068309

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772277B2