Ethanol, 2-(aminooxy)-, hydrochloride → 1-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone O-(2-hydroxy-ethyl)-oxime

HRID 1959677Notizen

Reaktionsgleichung

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22](=O)[CH3:23])[N:20]=2)[N:15]=[N:14]1.Cl.[NH2:26][O:27][CH2:28][CH2:29][OH:30]>CO>[OH:30][CH2:29][CH2:28][O:27][N:26]=[C:22]([C:19]1[N:20]=[C:21]2[N:13]([CH2:12][C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][C:2]=3[F:1])[N:9]=[CH:8][CH:7]=[CH:6]4)[N:14]=[N:15][C:16]2=[N:17][CH:18]=1)[CH3:23]

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

To a solution of 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (190.0 mg, 0.59 mmol) in MeOH (40 mL) was added 2-(aminooxy)ethanol hydrochloride (134.0 mg, 1.18 mol). The mixture was heated at 45° C. overnight. The solvent was removed under reduced pressure. The residue was purified by column chromatography with gradient (DCM:MeOH=10:1) to give the title compound as a white solid (168.0 mg, 71%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.30 (s, 1H), 8.93 (d, 1H), 8.41 (d, 1H), 8.19 (d, 1H), 7.83 (d, 1H), 7.54 (dd, 1H), 6.24 (s, 2H), 4.78 (t, 1H), 4.31 (t, 2H), 3.72 (m, 2H), 2.29 (s, 3H). LCMS (method A): [MH]+=382, tR=4.99 min.

Aufarbeitung

customThe solvent was removed under reduced pressure
customThe residue was purified by column chromatography with gradient (DCM:MeOH=10:1)

Quellen und Nachweise

ORD-Eintrag: ord-7c5e6568e5ae44ce86f3ba3a3131d651
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08410264B2

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