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Tetrahydrofuran → 3-(4-(2-(Fluoro-phenoxy)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine

HRID 640322
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 640322
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:6][C:7]1[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]C(Cl)=NO)=CC=1.C([C:27]1[C:28]([NH2:33])=[N:29][CH:30]=[CH:31][CH:32]=1)#C.[CH2:34]([N:36](CC)CC)C>O>[F:6][C:7]1[CH:24]=[CH:23][CH:22]=[CH:21][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:16][C:2]=1[CH2:3][C:4]1[CH:34]=[N:36][O:1][C:5]=1[C:27]1[C:28]([NH2:33])=[N:29][CH:30]=[CH:31][CH:32]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 124225263-Ethynylpyridin-2-amineHCID 72262883(4-(2-Fluoro-phenoxy)-phenyl)acetohydroximoyl chloride

Produkt 1

HCID 866124583-(4-(2-(Fluoro-phenoxy)-benzyl)-isoxazol-5-yl)-pyridin-2-ylamineAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a tetrahydrofuran (10.0 mL) solution of (4-(2-fluoro-phenoxy)-phenyl)-acetohydroximoyl chloride (290 mg, 1.04 mmol) described in Manufacturing Example 83-1-3 and 3-ethynyl-pyridin-2-ylamine (50.0 mg, 0.423 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (177 μL, 1.27 mmol) at room temperature, which was stirred for 30 minutes at 60° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5) to obtain the title compound (57.0 mg, 37.3%).

Aufarbeitung

  1. extractionwhich was then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-ad73772e263a4ce592aed7b86332d7a8
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691882B2

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