Water → N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}-3-(trifluoromethyl)benzamide

HRID 1874535Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.O>N1C=CC=CC=1>[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:1][C:2]2[N:7]=[CH:6][C:5]([O:8][C:9]3[CH:10]=[C:11]([NH:15][C:16](=[O:27])[C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:24])[F:25])[CH:18]=4)[CH:12]=[CH:13][CH:14]=3)=[CH:4][CH:3]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-(trifluoromethyl)benzamide (2.00 g, 5.36 mmol) in pyridine (60 mL) was added under ice-cooling 4-methylbenzenesulfonyl chloride (1.12 g, 5.89 mmol), and the mixture was stirred with heating at 80° C. for 2 days. The reaction mixture was cooled to room temperature, water (200 mL) was added thereto and the mixture was extracted with ethyl acetate (300 mL). The organic layer was washed with saturated brine (300 mL), and dried over anhydrous sodium sulfate. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (2.75 g, 99%) as a yellow oil. The obtained compound was used in the next reaction without further purification.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate (300 mL)
washThe organic layer was washed with saturated brine (300 mL)
dry with materialdried over anhydrous sodium sulfate
customThe insoluble material was removed by filtration
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-d6718faae88f425887ac860dd4b0a40a
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Reaction notes

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