Acetic Acid → HCID 57448664, Verbindung

HRID 446673

Reaktionsgleichung

[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:10]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)(=[O:22])=[O:21])=[N:11][C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[C:4](Cl)[N:3]=1.CS(C)=O.C[O-].[Na+].[C:40](O)(=[O:42])C>CCOC(C)=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:10]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)(=[O:22])=[O:21])=[N:11][C:12]3[C:17]([N:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[C:4]([O:42][CH3:40])[N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a crude product of N-{3-[(2,6-dichloropyridin-4-yl)amino]quinoxalin-2-yl}-3-nitrobenzenesulfonamide (1.24 g) prepared using procedures similar to those for Example 151, was added anhydrous DMSO (10 mL), followed by sodium methoxide (273 mg). The resulting mixture was heated at 100° C. for 3 days. The mixture was diluted with EtOAc and water, and the pH was adjusted to about 4 by adding acetic acid. The product was extracted with EtOAc (3×). The combined extracts were washed with brine to give the crude product. A portion of the crude product was purified by prep HPLC to give N-(3-{[2-chloro-6-(methyloxy)pyridin-4-yl]amino}quinoxalin-2-yl)-3-nitrobenzenesulfonamide. 1H NMR (400 MHz, DMSO) δ 9.44 (s, 1H), 8.90 (s, 1H), 8.50 (d, 1H), 8.42 (d, 1H), 7.88-7.84 (m, 2H), 7.77 (s, 1H), 7.74 (s, 1H), 7.64 (d, 1H), 7.45-7.38 (m, 2H), 3.82 (s, 3H); MS (EI) m/z for C20H15ClN6O5S: 496.94 (MH+).

Aufarbeitung

extractionThe product was extracted with EtOAc (3×)
washThe combined extracts were washed with brine
customto give the crude product
customA portion of the crude product was purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag: ord-ee725ae26a1c4ee0ab0d766470fb3701
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08481001B2

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