4-(Trifluoromethoxy)benzylamine → 3-(3,5-Dibromo-4-hydroxyphenyl)-N-(4-(trifluoromethoxy)benzyl)-1,2,4-oxadiazole-5-carboxamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[N:14]=[C:13]([C:15]([O:17]CC)=O)[O:12][N:11]=2)[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].[F:20][C:21]([F:32])([F:31])[O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1>C(O)C>[Br:9][C:6]1[CH:5]=[C:4]([C:10]2[N:14]=[C:13]([C:15]([NH:28][CH2:27][C:26]3[CH:29]=[CH:30][C:23]([O:22][C:21]([F:20])([F:31])[F:32])=[CH:24][CH:25]=3)=[O:17])[O:12][N:11]=2)[CH:3]=[C:2]([Br:1])[C:7]=1[OH:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of the ethyl 3-(3,5-dibromo-4-hydroxyphenyl)-1,2,4-oxadiazole-5-carboxylate (78 mg, 0.2 mmol) plus 4-trifluoromethoxybenzyl amine (57 mg, 0.3 mmol) in ethanol (3 mL) was refluxed for 6 hours. The resulting solution was evaporated in vacuo and the residue was dissolved in ethyl acetate (2.5 mL) and washed with 1 N hydrochloric acid (2 mL), then water (2 mL). The organic layer was evaporated to dryness in vacuo and purified by preparative HPLC to give the title compound (57 mg, 53%) as a colourless powder. 1H NMR δ (ppm) (DMSO-d6): 4.55 (2 H, d), 7.38 (2 H, d), 7.51 (2 H, d), 10.07 (1 H, t), 10.95 (1 H, s, br). LCMS (10 cm_apci_formic) tR 4.14 min; m/z 534/536/538 [M−H]−.
Workup
- customThe resulting solution was evaporated in vacuo
- dissolutionthe residue was dissolved in ethyl acetate (2.5 mL)
- washwashed with 1 N hydrochloric acid (2 mL)
- customThe organic layer was evaporated to dryness in vacuo
- custompurified by preparative HPLC
Sources & evidence
- ORD record
- ord-55216fbb8c4849a78fe14d94191da941
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796321B2
Reaction notes
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