Benzo(d)thiazol-2-amine → 9-Bromo-5-(2-benzothiazolylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52557

Reaction equation

HRID 52557 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](O)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[NH2:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:21][C:22]3[S:23][C:24]4[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=4[N:26]=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 8706Benzo(d)thiazol-2-amineHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 544171439-Bromo-5-(2-benzothiazolylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 76.4%

Procedure

A procedure similar to that described in Example 52 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 2-aminobenzothiazole (80 mg, 0.53 mmol) to give 180 mg of the title compound (76%): mp 264°~265° C.; 1H NMR (270 MHz, DMSO-d6) δ12.46 (bs, 1H), 12.09 (s, 1H), 7.99 (d, 1H, J=7.9 Hz), 7.74 (d, 2H, J=7.9 Hz), 7.44 (dt, 1H, J=1.3, 7.9 Hz), 7.31 (dt, 1H, J=1.3, 7.9 Hz), 7.25 (s, 1H), 7.19 (s, 1H), 5.21~5.31 (m, 1H), 3.04 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.69~2.91 (m, 3H), 2.09 (dm, 1H, J=13.5 Hz), 1.85~1.99 (m, 1H).

Sources & evidence

ORD record
ord-0f0f381bc3854233b852572920b644f4
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Linked notes

Loading…