Tetrahydrofuran → 3-(3-(4-Phenylamino-benzyl)-isoxazol-5-yl)-pyridin-2-ylamine
Reaktionsgleichung
O1CCCC1.[C:6]1([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20](Cl)=[N:21][OH:22])=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:24]([C:26]1[C:27]([NH2:32])=[N:28][CH:29]=[CH:30][CH:31]=1)#[CH:25].C(N(CC)CC)C>O>[C:6]1([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]4[C:27]([NH2:32])=[N:28][CH:29]=[CH:30][CH:31]=4)[O:22][N:21]=3)=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a tetrahydrofuran (3 mL) solution of (4-phenylamino-phenyl)-acetohydroximoyl chloride (150 mg, 0.576 mmol) described in Manufacturing Example 69-1-4 and 3-ethynyl-pyridin-2-ylamine (43 mg, 0.367 mmol) described in Manufacturing Example 1-2-3 was added triethylamine (201 μL, 1.44 mmol) at room temperature, which was stirred for 7 hours at 50° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (48 mg, 24%).
Aufarbeitung
- extractionwhich was then extracted with ethyl acetate
- washThe organic layer was washed with water and saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under a reduced pressure
- customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=4:1-2:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-44e1be6aa2104997b2f8ab7d26d98ed1
- Quelldatensatz
- uspto-grants-2013_08
- Patentnummer
- US08507530B2
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