Pyridine → 1,3-dimethyl-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide

HRID 1874323Notes

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[N:22]([CH3:23])[N:21]=[C:20]([CH3:24])[CH: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>O>[CH3:23][N:22]1[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:19][C:20]([CH3:24])=[N:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (750 mg, 2.32 mmol), p-toluenesulfonyl chloride (486 mg, 2.55 mmol) and pyridine (6 mL) was stirred at 80° C. for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure and dried to give the title compound (1.13 g, 99%) as a colorless oil.

Workup

extractionextracted with ethyl acetate (×3)
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
concentrationThe filtrate was concentrated under reduced pressure
customdried

Sources & evidence

ORD record: ord-bca46c3900ab4778a4323eca0e94f9d6
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Reaction notes

Loading…