Ethyl isothiocyanatoformate → Ethyl{[5-(3-{[(3-methylpyridin-2-yl)carbonyl]amino}phenoxy)pyridin-2-yl]carbamothioyl}carbamate

HRID 1874386

Reaktionsgleichung

Reaktionsgleichung von HRID 1874386
[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[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:17])[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]=[S:27]>CS(C)=O.O>[CH3:24][C:23]1[C:18]([C:16]([NH:15][C:11]2[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=2)[O:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:26]([NH:25][C:28](=[O:29])[O:30][CH2:31][CH3:32])=[S:27])=[N:7][CH:6]=2)=[O:17])=[N:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 2

HCID 85320Ethyl isothiocyanatoformateHCID 57749261N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

Produkt 1

HCID 57749212Ethyl{[5-(3-{[(3-methylpyridin-2-yl)carbonyl]amino}phenoxy)pyridin-2-yl]carbamothioyl}carbamateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of N-{3-[(6-aminopyridin-3-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide (1.84 g, 5.75 mmol) in DMSO (20 mL) was added dropwise with stirring under ice-cooling ethyl isothiocyanatoformate (0.75 mL, 6.35 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (25%→40% ethyl acetate-hexane) to give the title compound (2.00 g, 77%) as a white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (25%→40% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3795b2873aec4fbaa8e079af334202c1
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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