1,1'-Carbonyldiimidazole → 3-Fluoro-N-methoxy-N-methylpicolinamide

HRID 573348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573348
[F:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:24][NH:25][O:26][CH3:27].CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[C:3]([C:8]([N:25]([O:26][CH3:27])[CH3:24])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27627863-Fluoropyridine-2-carboxylic acid

Produkt 1

HCID 866889893-Fluoro-N-methoxy-N-methylpicolinamideAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 3-fluoropicolinic acid (17.7 g) in THF (300 mL) was added CDI (22.4 g) at room temperature, and the mixture was stirred at room temperature for 30 min and heated to 50° C. After stirring at 50° C. for 1 h, the mixture was cooled to room temperature. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (18.4 g) and DIPEA (32.9 mL) at room temperature, and the mixture was stirred at room temperature for 12 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt) to give the title compound (21.8 g).

Aufarbeitung

  1. temperatureheated to 50° C
  2. stirringAfter stirring at 50° C. for 1 h
  3. temperaturethe mixture was cooled to room temperature
  4. stirringthe mixture was stirred at room temperature for 12 h
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-2b5f36724e144136bb7fb640ab418644
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029536B2

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