1-Hydroxybenzotriazole → 3-(4-(tert-butyl)phenyl)-5-(5-methyl-1H-1,2,4-triazol-3-yl)-1,2,4-oxadiazole

5-Methyl-1H-1,2,4-triazole-3-carboxylic acid (200 mg, 1.57 mmol), EDC.HCl (360 mg, 1.89 mmol), and HOBT (255 mg, 1.89 mmol) were dissolved in DMF (15 mL) and the solution was stirred at RT for 30 min. 4-(tert-Butyl)-N-hydroxybenzimidamide (363 mg, 1.89 mmol) was added and the reaction was stirred at RT for 1 h and then at 140° C. for an additional 2 h. The reaction mixture was cooled to RT, and diluted with H2O (100 mL) and EtOAc (100 mL). The organic layer was separated, washed with H2O (2×50 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product which was purified by silica gel chromatography (EtOAc/Hexane 12%-100% EtOAc) to afford 3-(4-(tert-butyl)phenyl)-5-(5-methyl-1H-1,2,4-triazol-3-yl)-1,2,4-oxadiazole as a yellow solid (210 mg, 47%). MS (ES+) C15H17N5O requires: 283. found 284 [M+H]+; 1H NMR (600 MHz, CDCl3) δ 8.02 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 2.50 (s, 3H), 1.34 (s, 9H).

1. stirringthe reaction was stirred at RT for 1 h
2. waitat 140° C. for an additional 2 h
3. temperatureThe reaction mixture was cooled to RT
4. customThe organic layer was separated
5. washwashed with H2O (2×50 mL) and brine (25 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto afford the crude product which
10. customwas purified by silica gel chromatography (EtOAc/Hexane 12%-100% EtOAc)

ORD record

ord-4a89d5b11a97450fb4609fccd79da53f

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018380B2