Ethyl 2-aminobenzoate → trans-9-Bromo-5-(o-ethoxycarbonylphenylcarbamoylmethyl)-6-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52537

反応式

HRID 52537 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][C@@H:15]([CH3:17])[C@H:14]([CH2:18][C:19](O)=[O:20])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH2:22]([O:24][C:25]([C:27]1[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=1[NH2:29])=[O:26])[CH3:23]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][C@@H:15]([CH3:17])[C@H:14]([CH2:18][C:19](=[O:20])[NH:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[C:25]([O:24][CH2:22][CH3:23])=[O:26])[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 6877Ethyl 2-aminobenzoateHCID 67885997trans-9-bromo-5-carboxymethyl-6-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

生成物 1

HCID 67885855trans-9-Bromo-5-(o-ethoxycarbonylphenylcarbamoylmethyl)-6-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione収率 36%

実験手順

A procedure similar to that described in Example 52 was carried out with trans-9-bromo-5-carboxymethyl-6-methyl-6,7-dihydro- 1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione (300 mg, 0,849 mmol) and o-ethoxycarbonylaniline (147 mg, 0.891 mmol) to give 153 mg of the title compound (36%): mp 238°~248° C.; 1H NMR (270 MHz, DMSO-d6) δ11.39 (s, 1H), 11.31 (s, 1H), 8.66 (d, 2H, J=8.4 Hz), 8.04 (dd, 1H, J=8.4, 1.7 Hz), 7.55 (td, 1H, J=8.4, 1.7 Hz), 7.35 (d, 1H, J=1.9 Hz), 7.19 (d, 1H, J=1.9 Hz), 7.11 (td, 1H, J=8.4, 1.7 Hz), 5.19~5.29 (m, 1H), 4.37 (q, 2H, J=7.3 Hz), 3.29 (dd, 1H, J=17.0, 5.1 Hz), 2.97 (dd, 1H, J=14.5, 4.6 Hz), 2.55~2.70 (m, 3H), 1.40 (t, 3H, J=7.3 Hz), 0.88 (d, 3H, J=6.9 Hz).

出典と根拠

ORDレコード
ord-7331ac621470437e81d5bbdc6b46161f
出典データセット
uspto-grants-1997_04
特許番号
US05616586

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