Iodoacetamide → N-{3-[(1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874324

Reaktionsgleichung

Reaktionsgleichung von HRID 1874324
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:18]=[N:19][C:20]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:26])=[O:25])=[CH:21][CH:22]=3)[CH:11]=2)=[O:8])=[CH:5][C:4]([CH3:34])=[N:3]1.C(N(CC)C(C)C)(C)C.CN(C)C=O.I[CH2:50][C:51]([NH2:53])=[O:52]>O>[NH2:53][C:51](=[O:52])[CH2:50][N:19]1[C:20](=[N:23][S:24]([C:27]2[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=2)(=[O:25])=[O:26])[CH:21]=[CH:22][C:17]([O:16][C:12]2[CH:11]=[C:10]([NH:9][C:7]([C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:34])[CH:5]=3)=[O:8])[CH:15]=[CH:14][CH:13]=2)=[CH:18]1

Komponenten

6

Edukt 4

HCID 3727IodoacetamideHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 577491871,3-dimethyl-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide

Produkt 1

HCID 68987305N-{3-[(1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamideAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1,3-dimethyl-N-{3-[(6-{[(4-methylphenyl)sulfonyl]amino}pyridin-3-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide (1.11 g, 2.32 mmol), N,N-diisopropylethylamine (424 μL, 2.44 mmol) and N,N-dimethylformamide (7 mL) was stirred at room temperature for 2 hr, iodoacetamide (451 mg, 2.44 mmol) was added and the mixture was stirred at room temperature 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 the residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (883 mg, 71%) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 15 hr
  2. extractionextracted with ethyl acetate (×3)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. filtrationthe residue was collected by filtration
  8. washwashed with ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-582607d9332540ec9b4bfb8f83053473
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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