Water → 3-(1-cyanocyclopropyl)-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}benzamide

HRID 1800388

Reaktionsgleichung

Reaktionsgleichung von HRID 1800388
[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:28])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4([C:26]#[N:27])[CH2:25][CH2:24]4)[CH:18]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[CH3:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.O>N1C=CC=CC=1>[C:26]([C:23]1([C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=2)[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:36]([C:33]4[CH:34]=[CH:35][C:30]([CH3:29])=[CH:31][CH:32]=4)(=[O:38])=[O:37])=[CH:3][CH:4]=3)[CH:10]=2)=[O:28])[CH2:24][CH2:25]1)#[N:27]

Komponenten

5

Edukt 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 68416693N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide

Produkt 1

HCID 684178753-(1-cyanocyclopropyl)-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}benzamideAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide (2.0 g, 5.4 mmol) in pyridine (60 mL) was added 4-methylbenzenesulfonyl chloride (1.13 g, 5.94 mmol) under ice-cooling, and the mixture was stirred with heating at 80° C. for 2 days. After the reaction mixture was cooled to room temperature, water (200 mL) was added, and the mixture was extracted with ethyl acetate (400 mL). The organic layer was washed with saturated brine (200 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the obtained residue was washed with ethyl acetate and diisopropyl ether to give the title compound (2.61 g, 92%) as a colorless solid.

Aufarbeitung

  1. temperaturecooling
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. extractionthe mixture was extracted with ethyl acetate (400 mL)
  4. washThe organic layer was washed with saturated brine (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washthe obtained residue was washed with ethyl acetate and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2e45b4a7a1eb40f4849bc6d782309027
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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