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

HRID 52523Notes

Reaction equation

HRID 52523 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][CH:24]=[CH:25][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][CH:24]=[CH:25][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 21552-AminothiazoleHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 538222129-Bromo-5-(2-thiazolylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 88%

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 2-aminothiazole (60 mg, 0.60 mmol) to give 185 mg of the title compound (88%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.20 (s, 1H), 12.07 (s, 1H), 7.47 (d, 2H, J=3.6 Hz), 7.23 (d, 1H, J=3.6 Hz), 7.22 (bs, 1H), 7.17 (bs, 1H), 5.17~5.28 (m, 1H), 3.04 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.64~2.89 (m, 3H), 2.06 (dm, 1H, J=13.5 Hz), 1.81~1.97 (m, 1H).

Sources & evidence

ORD record
ord-1cdf649cf3b6478a9df361d3bd1620e1
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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