Benzylamine → 9-Bromo-5-benzylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52498

Reaction equation

HRID 52498 reaction equation
[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.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:20])[NH:28][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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 7504BenzylamineHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 536871739-Bromo-5-benzylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 90.2%

Procedure

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 benzylamine (54 μL, 0.5 mmol) to give 170 mg of the title compound (89%): mp 220°~223° C.; 1H NMR (270 MHz, DMSO-d6) δ12.04 (bs, 1H), 8.46~8.55 (m, 1H), 7.19~7.37 (m, 6H), 7.14 (d, 1H, J=2 Hz), 5.09~5.19 (m, 1H), 4.21~4.35 (m, 2H), 3.04 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.77 (dm, 1H, J=17.1 Hz), 2.41~2.54 (m, 2H), 2.00 (dm, 1H, J=13.5 Hz), 1.72~1.90 (m, 1H).

Sources & evidence

ORD record
ord-4e3f77efa824463fb33dd399669ef34b
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Linked notes

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