5-(5-Nitro-1H-pyrazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole → HCID 178507332, compound

HRID 2400535Notes

Reaction equation

HRID 2400535 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[N:10]=2)[CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[NH:8][N:7]=[C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([O:20][C:21]([F:22])([F:24])[F:23])=[CH:18][CH:19]=3)[N:10]=2)[CH:5]=1

Participants

4

Reactant 1

HCID 1361650555-(5-Nitro-1H-pyrazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole2×

Product 1

HCID 178507332HCID 178507332, compoundYield 103.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(5-nitro-1H-pyrazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole (Intermediate F, 342 mg, 1.0 mmol) in ethyl acetate (43 mL) was subjected to hydrogenation using an H-Cube flow reactor (Thales Nano, Budapest, Hungary) (10% Pd/C, 30×4 mm, 1 bar H2, 25° C., 1 mL/min). After evaporation of the solvent, the crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 1:1) affording the title compound as a solid (322 mg, 93%): 1H NMR (400 MHz, DMSO-d6) δ 12.49 (s, 1H), 8.19 (d, 2H), 7.49 (d, 2H), 5.93 (s, 1H), 5.44 (s, 2H); ES-MS m/z 312 (MH)+; HPLC RT (Method E) 1.76 min.

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-194ed59d55fe4ddc92a9ec279d25d338
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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