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

HRID 52529

반응식

HRID 52529 반응식
[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.[C:21]([NH:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)(=[O:23])[CH3:22]>>[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:27]=[CH:26][C:25]([NH:24][C:21](=[O:23])[CH3:22])=[CH:31][CH:30]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

참가 물질

3

반응물 2

HCID 312304-AminoacetanilideHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

생성물 1

HCID 442853949-Bromo-5-(p-acetylaminophenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione수율 91.6%

실험 절차

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-acetylaminoaniline (75 mg, 0.5 mmol) to give 190 mg of the title compound (91%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.06 (s, 1H), 9.94 (s, 1H), 9.87 (s, 1H), 7.44~7.52 (m, 4H), 7.23 (bs, 1H), 7.17 (bs, 1H), 5.18~5.26 (m, 1H), 3.07 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1 Hz), 2.55~2.64 (m, 2H), 2.10 (dm, 1H, J=13.5 Hz), 2.02 (s, 3H), 1.80~1.96 (m, 1H).

출처 및 근거

ORD 기록
ord-2d3fe4f613654e8a912dc2b3099779fb
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616586

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