Lithium Hydroxide → 2-(Difluoromethyl)-5-(isobutyramidomethyl)nicotinic acid

HRID 1469797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469797
[F:1][CH:2]([F:21])[C:3]1[N:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:10][C:4]=1[C:5]([O:7]CC)=[O:6].[Li+].[OH-]>O1CCOCC1.O>[F:21][CH:2]([F:1])[C:3]1[N:13]=[CH:12][C:11]([CH2:14][NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:10][C:4]=1[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 71059744Ethyl 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinate

Produkt 1

HCID 710598402-(Difluoromethyl)-5-(isobutyramidomethyl)nicotinic acidAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(difluoromethyl)-5-(isobutyramidomethyl)nicotinate (200 mg, 0.66 mmol) in 1,4-Dioxane was added a solution of LiOH (70 mg, 1.66 mmol) in H2O (1 mL) and the reaction mixture was stirred at rt for 1 h. Then the reaction mixture was quenched with 1N HCl and the precipitated solid was filtered and dried to afford 150 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 13.98 (br s, 1H), 8.72 (s, 1H), 8.45 (t, 1H), 8.17 (s, 1H), 7.67-7.32 (t, J=54 Hz, 1H), 4.39-4.37 (d, J=5.7 Hz, 2H), 2.43 (m, 1H), 1.04-1.02 (d, J=6.6 Hz, 6H).

Aufarbeitung

  1. customThen the reaction mixture was quenched with 1N HCl
  2. filtrationthe precipitated solid was filtered
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-899338ff0e1a4ce2b13d6d88e2de94ca
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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