4-Toluenesulfonyl chloride → 2-(5-Benzyl-1,3,4-oxadiazol-2-yl)-6-bromo-5-(trifluoromethyl)pyridin-3-amine

HRID 574207Notes

Reaction equation

[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]=1

Participants

Conditions

Temperature: 65 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-cd112c33554646009fa9673a92848a89
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034879B2

Reaction notes

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