Hydrogen Bromide → HCID 66732172, Verbindung

HRID 1963460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963460
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][N:10]2C(OC)=O)=[CH:4][C:3]=1[F:25].Br>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C@H:9]2[CH2:14][C@H:13]([C:15]3[O:19][NH:18][C:17](=[O:20])[CH:16]=3)[CH2:12][CH2:11][NH:10]2)=[CH:4][C:3]=1[F:25]

Komponenten

3

Edukt 2

HCID 260Hydrogen BromideHCID 131730423HCID 131730423, Verbindung

Produkt 1

HCID 66732172HCID 66732172, VerbindungAusbeute 19,7 %

Versuchsvorschrift

Trans-methyl 2-(4-chloro-3,5-difluorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (157 mg, 0.42 mmol) was dissolved in hydrogen bromide (33% in acetic acid, 3.32 mL, 18.95 mmol) and stirred at room temperature for 16 h. The solvent was evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-(trans-2-(4-chloro-3,5-difluorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (26 mg, 19%). 1H NMR (600 MHz, dmso) δ 1.75-2.11 (m, 4H), 2.66-2.77 (m, 1H), 2.81-2.95 (m, 1H), 3.14 (s, br., 1H), 3.86 (s, br., 1H), 6.03 (s, 1H), 7.32-7.42 (m, 2H). HRMS Calculated for [C14H13ClF2N2O2+H]+: 315.0712. Found: 315.0715

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm)

Quellen und Nachweise

ORD-Eintrag
ord-a7a7a9d16c9e4715b12e674f328336a7
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415378B2

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