Dichloromethane → 5-(3-Methoxycarbonyl-5-trifluoromethoxyphenyl)-3-(2-pyridyl)-1,2,4-oxadiazole
Reaction equation
[C:1]([C:3]1[CH:4]=C(C=C(OC(F)(F)F)C=1)C(O)=O)#[N:2].[NH:17]=[C:18]([O:33]C)[C:19]1[CH:20]=[C:21]([CH:25]=[C:26]([O:28][C:29]([F:32])([F:31])[F:30])[CH:27]=1)[C:22]([OH:24])=[O:23].[C:35](Cl)(=O)[C:36](Cl)=O.[CH2:41]([N:43](CC)CC)C.Cl[CH2:49]Cl>CN(C)C=O>[CH3:49][O:24][C:22]([C:21]1[CH:20]=[C:19]([C:18]2[O:33][N:43]=[C:41]([C:36]3[CH:35]=[CH:4][CH:3]=[CH:1][N:2]=3)[N:17]=2)[CH:27]=[C:26]([O:28][C:29]([F:30])([F:31])[F:32])[CH:25]=1)=[O:23]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 1.2 mg (1.5%) of 5-(3-methoxycarbonyl-5-trifluoromethoxyphenyl)-3-(2-pyridyl)-1,2,4-oxadiazole [1H-NMR (CDCl3), δ (ppm): 8.86 (d, w, 2H), 8.36 (s, 1H), 8.25 (d, 1H), 8.15 (s, 1H), 7.90 (t, 1H), 7.51 (m, 1H), 4.01 (s, 3H)].
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-5797f287752940398ec4460bb6044154
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06660753B2
Reaction notes
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