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

HRID 52541

反応式

HRID 52541 の反応式
[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.[CH:21]1[C:26]([NH2:27])=[CH:25][CH:24]=[C:23]([NH2:28])[CH:22]=1>>[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:21]=[CH:22][C:23]([NH2:28])=[CH:24][CH:25]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

参加物

3

反応物 2

HCID 7814P-PhenylenediamineHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

生成物 1

HCID 442853959-Bromo-5-(p-aminophenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione収率 61%

実験手順

A procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (150 mg, 0.44 mmol) and p-phenylenediamine (540 mg, 5 mmol) to give 115 mg of the title compound (61%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.11 (s, 1H), 10.32 (s, 1H), 9.93 (br, 2H), 7.67 (d, 1H, J=8.9 Hz), 7.29 (d, 2H, J=8.6 Hz), 7.50 (dd, 2H, J=8.6 Hz), 7.23 (bs, 1H), 7.20 (bs, 1H), 5.18~5.27 (m, 1H), 3.08 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1 Hz), 2.56~2.70 (m, 2H), 2.08 (dm, 1H, J=13.5 Hz), 1.82~1.96 (m, 1H).

出典と根拠

ORDレコード
ord-ce19e66f37904955a9087a134d90615c
出典データセット
uspto-grants-1997_04
特許番号
US05616586

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