Tetrahydrofuran → 2-{4-[(3-Fluoro-4-methylphenyl)oxy]phenyl}ethyl imidocarbamate

HRID 705914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705914
Cl[C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:21])=[CH:15][CH:14]=2)=N[C:7]=1C(F)(F)F.[N:22]#[C:23][NH2:24].OS([C:29]([F:32])(F)F)(=O)=O.[CH2:33]1COCC1>>[C:23](=[NH:24])([O:21][CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][C:5]2[CH:4]=[CH:3][C:2]([CH3:7])=[C:29]([F:32])[CH:33]=2)=[CH:18][CH:17]=1)[NH2:22]

Komponenten

5

Edukt 4

HCID 8028TetrahydrofuranHCID 9864CyanamideHCID 62406Trifluoromethanesulfonic acidHCID 677738582-(4-((5-Chloro-6-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)ethanol

Produkt 1

HCID 677758982-{4-[(3-Fluoro-4-methylphenyl)oxy]phenyl}ethyl imidocarbamateAusbeute 84 %

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of 2-(4-((5-chloro-6-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)ethanol (0.2 g, 0.630 mmol) and cyanamide (0.053 g, 1.259 mmol) in dry THF (3 mL) under nitrogen was added triflic acid (0.112 mL, 1.259 mmol). The mixture was heated at 55° C. for 1 h. Purification via reverse phase flash chromatography afforded the title compound (250 mg, 0.529 mmol, 84% yield) as a white solid. LCMS: rt=2.77 min, [M+H+]=360

Aufarbeitung

  1. customPurification via reverse phase flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dcc2a7ac65864f0b84457e29573ec0bf
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174968B2

Notizen zur Reaktion

Wird geladen…