4-Toluenesulfonyl chloride → 6-methyl-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}pyridine-2-carboxamide

HRID 1874390Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-6-methylpyridine-2-carboxamide (10.41 g, 32.5 mmol), p-toluenesulfonyl chloride (6.83 g, 35.8 mmol) and pyridine (75 mL) was stirred at 80° C. for 2 hr. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate-hexane to give the title compound (14.8 g, 96%) as a pale-brown solid.

Workup

concentrationThe reaction solution was concentrated under reduced pressure, and ethyl acetate
additionwas added to the residue
washThe mixture was washed with aqueous sodium hydrogen carbonate solution, water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
concentrationThe filtrate was concentrated under reduced pressure
washthe residue was washed with ethyl acetate-hexane

Sources & evidence

ORD record: ord-7adb8561eba945ae86b19831f7069006
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Reaction notes

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