Trifluoroacetic acid → 3-(1-methyl-5-nitro-1H-pyrazol-3-yl)-1,2,4-oxadiazole

To a solution of N′-hydroxy-1-methyl-5-nitro-1H-pyrazole-3-carboximidamide (1.66 g, 8.97 mmol) and trimethoxymethane (17.6 mL, 161 mmol) in MeOH (2.8 mL) was added 2,2,2-trifluoroacetic acid (0.35 mL, 4.48 mmol) and the mixture was refluxed for about 1 h. The reaction was cooled to ambient temperature and continued to stir for about 16 h. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between DCM (25 mL) and saturated NaHCO3 (10 mL). The aqueous layer was back extracted with DCM (25 mL). The combined organic layers were washed with brine (10 mL), dried over MgSO4, filtered and concentrated under reduced pressure to afford 3-(1-methyl-5-nitro-1H-pyrazol-3-yl)-1,2,4-oxadiazole (1.75 g, 8.97 mmol, 100%, which was used without further purification). LC-MS (Table 1, Method g) Rt=1.56 min, m/z 196 (M+H)+. 1H-NMR (DMSO-d6, Bruker 400 MHz) 9.79 (s, 1H), 7.72 (s, 1H), 4.27 (s, 3H).

1. temperaturethe mixture was refluxed for about 1 h
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. customthe residue was partitioned between DCM (25 mL) and saturated NaHCO3 (10 mL)
4. extractionThe aqueous layer was back extracted with DCM (25 mL)
5. washThe combined organic layers were washed with brine (10 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-a1b87f1730784cad8a14fc824370cd76

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150592B2