Acetic Acid → HCID 57448664, compound

HRID 1669946

Reaction equation

[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

Participants

Conditions

Temperature: 100 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-75970cdf5863464d873accfc25e7ebef
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989622B2

Linked notes

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