Tetrahydrofuran → 5-(3-(6-Phenoxy-pyridin-3-ylmethyl)-isoxazol-5-yl)-pyridin-2-ylamine
Reaktionsgleichung
O1CCCC1.[C:6]([C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1)#[CH:7].[O:15]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](Cl)=[N:30][OH:31])=[CH:24][N:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>O>[O:15]([C:22]1[N:23]=[CH:24][C:25]([CH2:28][C:29]2[CH:7]=[C:6]([C:8]3[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=3)[O:31][N:30]=2)=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a tetrahydrofuran (2 mL) solution of 5-ethynyl-pyridin-2-ylamine (30 mg, 0.25 mmol) described in Manufacturing Example 28-1-3 were added (2-phenoxy-pyridin-5-yl)acetohydroximoyl chloride (100 mg, 0.381 mmol) described in Manufacturing Example 40-1-4 and triethylamine (70.8 μL, 0.508 mmol), which was stirred for 8 hours at 50° C. Water was added to the reaction mixture at room temperature, which was extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (26 mg, 30%).
Aufarbeitung
- extractionwhich was extracted with ethyl acetate
- customThe organic layer was separated
- washwashed with saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under a reduced pressure
- customthe residue was purified by NH silica gel column chromatography (ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-b29de8cc213442428c1029686deb49f7
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08153662B2
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