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Ethyl Acetate → 2,5-Difluoro-N-methoxy-N-methylnicotinamide

HRID 715916
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 715916
[F:1][C:2]1[C:7]([C:8](O)=[O:9])=[CH:6][C:5]([F:11])=[CH:4][N:3]=1.Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:25][NH:26][O:27][CH3:28].C(OCC)(=O)C>CN(C)C=O.C(N(C(C)C)CC)(C)C.ON1C2C=CC=CC=2N=N1.O>[F:1][C:2]1[C:7]([C:8]([N:26]([O:27][CH3:28])[CH3:25])=[O:9])=[CH:6][C:5]([F:11])=[CH:4][N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 8857Ethyl AcetateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 118159992,5-difluoropyridine-3-carboxylic Acid

Produkt 1

HCID 916189642,5-Difluoro-N-methoxy-N-methylnicotinamideAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 757711-HydroxybenzotriazoleKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

To a solution of 2,5-difluoropyridine-3-carboxylic acid (3.00 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (4.34 g), 1-hydroxybenzotriazole (127 mg), and N,O-dimethylhydroxylamine hydrochloride (1.93 g) in N,N-dimethylformamide (30 ml), diisopropylethylamine (7.42 ml) was added, and the mixture was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution to separate the aqueous and organic layers. The aqueous layer was subjected to extraction with ethyl acetate. The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain the title compound (2.42 g).

Aufarbeitung

  1. customto separate the aqueous and organic layers
  2. extractionThe aqueous layer was subjected to extraction with ethyl acetate
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-264b2750b84c4af2b44b8bbf3e1a064d
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09187489B2

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