Potassium Carbonate → 5-(2-(Quinolin-4-yl)methoxyphenyl)-N-(3-trifluoromethylphenyl)-1,3,4-oxadiazol-2-amine

HRID 558176Notes

Reaction equation

[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[O:14][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[OH:21])=[N:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.Cl[CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[N:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26]([CH2:25][O:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:13]2[O:14][C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:22])([F:1])[F:23])[CH:4]=3)=[N:11][N:12]=2)=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(5-(3-trifluoromethylphenylamino)-1,3,4-oxadiazol-2-yl) phenol (100 mg, 0.31 mmol; Reference Compound 9-(1)) and 4-chloromethylquinoline (55 mg, 0.31 mmol) in N,N-dimethylformamide (1.0 mL) was added potassium carbonate (86 mg, 0.62 mmol) at room temperature and then the mixture was stirred at 60° C. over night. The reaction solution was cooled to a room temperature and diluted with ethyl acetate (100 mL). The ethyl acetate solution was washed with a saturated brine solution (30 mL), dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The residue was purified with a silica gel column chromatography (hexane/ethyl acetate) to give 39 mg (27%) of the titled compound as a colorless solid.

Workup

temperatureThe reaction solution was cooled to a room temperature
washThe ethyl acetate solution was washed with a saturated brine solution (30 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under a reduced pressure
customThe residue was purified with a silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-fe80f13933c74b7091215f7ef9d86aff
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063034B2

Reaction notes

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