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

HRID 52507Notes

Reaction equation

HRID 52507 reaction equation
[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][C:28]([NH2:29])=[CH:27][CH:26]=1)(=[O:24])(=[O:23])[NH2:22]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:20])[NH:29][C:28]3[CH:30]=[CH:31][C:25]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:26][CH:27]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

3

Reactant 2

HCID 5333SulfanilamideHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 540036919-Bromo-5-(p-sulfamoylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 77%

Procedure

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 (170 mg, 0.5 mmol) and p-sulfamoylaniline (87 mg, 0.506 mmol) to give 190 mg of the title compound (77%): mp 263°~267° C.; 1H NMR (270 MHz, DMSO-d6) δ12.07 (s, 1H), 10.21 (s, 1H), 8.20 (bs, 1H), 7.81 (d, 1H, J=8.0 Hz), 7.63 (d, 1H, J=8.0 Hz), 7.24 (bs, 2H), 7.19 (bs, 2H), 5.17~5.28 (m, 1H), 3.06 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=16.8 Hz), 2.55~2.70 (m, 2H), 2.12 (dm, 1H, J=13.5 Hz), 1.80~1.97 (m, 1H).

Sources & evidence

ORD record
ord-eb4801bc9b3e421a96defd10ea887e38
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

Loading…