2-Aminobenzenesulfonamide → 9-Bromo-5-(o-sulfamoylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52505

Reaktionsgleichung

Reaktionsgleichung von HRID 52505
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([OH:20])=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[S:21]([C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27])(=[O:24])(=[O:23])[NH2:22]>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:20])[NH:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[S:21](=[O:24])(=[O:23])[NH2:22])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Komponenten

4

Edukt 2

HCID 728942-AminobenzenesulfonamideHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Produkt 1

HCID 542862299-Bromo-5-(o-sulfamoylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneAusbeute 17,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22609514Ethyl acetate acetateLösungsmittel

Versuchsvorschrift

A procedure similar to that described in Example 51 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (340 mg, 1 mmol) and o-sulfamoylaniline (180 mg, 1.05 mmol) to give 85 mg of the title compound (17%) after silica gel column chromatography of the crude product with 1% acetic acid/ethyl acetate as an eluent: mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.06 (bs, 1H), 9.36 (s, 1H), 8.01 (d, 1H, J=8.1 Hz), 7.85 (d, 2H, J=8.1 Hz), 7.60 (t, 1H, J=8.1 Hz), 7.58 (s, 2H), 7.32 (t, 1H, J=8.1 Hz), 7.23 (d, 1H, J=2 Hz), 7.16 (d, 1H, J=2 Hz), 5.17~5.27 (m, 1H), 3.07 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.82 (dm, 1H, J=17.1 Hz), 2.71~2.76 (m, 2H), 2.12 (dm, 1H, J=13.5 Hz), 1.78~1.96 (m, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-d2b7a75e8fc04a84bb65c577c3a1f451
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616586

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