Dimethylformamide → 5-(3-Cyano-5-trifluoromethoxyphenyl)-3-(2-pyridyl)-1,2,4-oxadiazole
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][C:13]([F:16])([F:15])[F:14])[CH:11]=1)C(O)=O)#[N:2].[NH:17]=[C:18](OC)[C:19]1C=C([CH:25]=[C:26](OC(F)(F)F)[CH:27]=1)C(O)=O.C(Cl)(=O)C(Cl)=O.C([N:43](CC)CC)C.[CH3:48][N:49](C)[CH:50]=[O:51]>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([C:50]2[O:51][N:43]=[C:48]([C:25]3[CH:26]=[CH:27][CH:19]=[CH:18][N:17]=3)[N:49]=2)[CH:9]=[C:10]([O:12][C:13]([F:14])([F:15])[F:16])[CH:11]=1)#[N:2]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-cyano-5-trifluoromethoxybenzoic acid, which 3-[imino(methoxy)methyl]-5-trifluoromethoxybenzoic acid (3:1, 50 mg, 0.2165 mmoles) in dichloromethane (1 mL) was treated with 2M oxalyl chloride (0.433 ml, 0.866 mmol, dichloromethane). The mixture was stirred 3 hours at room temperature. The solvent and excess reagent were removed in vacuo. The residue was treated with 2-pyridyl-amidoxime (29.7 mg, 0.216 mmol) and triethylamine (87 mg, 0.866 mmol) in dichloromethane (1 mL). The mixture was then heated in dimethylformamide (0.5 mL) for 3 hours at 120° C. Standard work up, purified by prep HPLC (C18 column, CH3CN:H2O=60:40), afforded 3.2 mg (4.5%) of 5-(3-Cyano-5-trifluoromethoxyphenyl)-3-(2-pyridyl)-1,2,4-oxadiazole [1H-NMR (CDCl3), δ (ppm): 8.86 (w, 1H), 8.56 (s, 1H), 8.40 (s, 1H)1 8.24 (d, 1H), 7.92 (t, 1H), 7.72 (s, 1H), 7.73 (m, 1H)].
Workup
- customThe solvent and excess reagent were removed in vacuo
- customStandard work up, purified by prep HPLC (C18 column, CH3CN:H2O=60:40)
Sources & evidence
- ORD record
- ord-7e0292ffc1a549faa93c0fd51429fc7e
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07112595B2
Reaction notes
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