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

HRID 1874387

Reaktionsgleichung

Reaktionsgleichung von HRID 1874387
[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](C)[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=C[CH:37]=1>>[CH3:37][C:23]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])=[N:19][CH:20]=[CH:21][CH:22]=1

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 57749288N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-6-methylpyridine-2-carboxamide

Produkt 1

HCID 577493583-methyl-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}pyridine-2-carboxamideAusbeute 99 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-6-methylpyridine-2-carboxamide (8.25 g, 25.8 mmol), p-toluenesulfonyl chloride (5.41 g, 28.4 mmol) and pyridine (50 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 (12.1 g, 99%) as a pale-brown solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-edc7c2f83e504d17ae0b988c5ac5dc24
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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