4-Toluenesulfonyl chloride → 2-(5-Benzyl-1,3,4-oxadiazol-2-yl)-6-bromo-5-(trifluoromethyl)pyridin-3-amine
Reaktionsgleichung
[NH2:1][C:2]1[C:3]([C:13]([NH:15][NH:16][C:17](=O)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:14])=[N:4][C:5]([Br:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)(Cl)Cl>[CH2:18]([C:17]1[O:14][C:13]([C:3]2[C:2]([NH2:1])=[CH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[C:5]([Br:12])[N:4]=2)=[N:15][N:16]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
To a stirred suspension of 3-amino-6-bromo-N′-(2-phenylacetyl)-5-(trifluoromethyl) picolinohydrazide (106 mg, 0.254 mmol) in CHCl3 (2 ml) was added TEA (142 ul, 1.016 mmol) followed by TsCl (145 mg, 0.762 mmol). The mixture was heated to 65° C. for 3 h. The solvent was removed in vacuo and the resulting brown residue was suspended in EtOAc (10 ml). The mixture was washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 85% iso-hexane/EtOAc to afford the title compound as a yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 7.85 (1H, s), 7.39 (4H, m), 7.30 (3H, m), 4.45 (2H, s). LC-MS Rt=5.84 min [M+H]+ 401.0 Method 10minLC_v002.
Aufarbeitung
- customThe solvent was removed in vacuo
- washThe mixture was washed with brine (10 ml)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe crude product was purified by chromatography on silica eluting with 85% iso-hexane/EtOAc
Quellen und Nachweise
- ORD-Eintrag
- ord-cd112c33554646009fa9673a92848a89
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09034879B2
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