Cyanamide → 2-(3-Fluoro-4-{[6-(trifluoromethyl)-2-pyridinyl]oxy}phenyl)ethyl imidocarbamate

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Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]([CH2:19][CH2:20][OH:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]=1.[N:22]#[C:23][NH2:24].OS(C(F)(F)F)(=O)=O>C1COCC1>[C:23](=[NH:22])([O:21][CH2:20][CH2:19][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[N:10]=2)=[C:2]([F:1])[CH:3]=1)[NH2:24]

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

To a solution of 2-(3-fluoro-4-{[6-(trifluoromethyl)-2-pyridinyl]oxy}phenyl)ethanol (70 mg, 0.232 mmol) and cyanamide (11.72 mg, 0.279 mmol) in THF (5 mL) was added triflic acid (0.025 mL, 0.279 mmol) under argon. The mixture was heated at 55° C. for 3 h. Purification via reverse phase flash chromatography then afforded the title compound (50 mg, 0.102 mmol, 43.7% yield). LCMS: rt=2.53 min, [M+H+]=344

Aufarbeitung

customPurification via reverse phase flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-39c4706cd7054cdf9f7d2aaa86894334
Quelldatensatz: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08637536B2

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