Aniline → 9-Bromo-5-methyl-5-phenylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52540Notes

Reaction equation

HRID 52540 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C:14]([CH2:18][C:19]([OH:21])=O)([CH3:17])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][C:14]([CH3:17])([CH2:18][C:19](=[O:21])[NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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 6115AnilineHCID 540544279-bromo-5-carboxymethyl-5-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 537441289-Bromo-5-methyl-5-phenylcarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 74.2%

Procedure

A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-5-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (100 mg, 0.28 mmol) and aniline (28 μL, 0.31 mmol) to give 89 mg of the title compound (73%): mp 155°~162° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ812.00 (s, 1H), 9.92 (s, 1H), 7.46 (d, 2H, J=8 Hz), 7.23 (t, 2H, J=8 Hz), 7.14 (bs, 2H), 6.99 (t, 1H, J=8 Hz), 3.63 (d, 1H, J=15 Hz), 2.90 (d, 1H, J=15 Hz), 2.80~2.90 (m, 2H), 2.25~2.40 (m, 1H), 1.85~2.00 (m, 1H), 1.68 (s, 3H).

Sources & evidence

ORD record
ord-c900e6a768a542c186872739c2fb95ab
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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