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

HRID 474675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474675
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-2f2472fdad554a4d8dfdc785bcf36596
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637536B2

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