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

HRID 52536Notes

Reaction equation

HRID 52536 reaction equation
[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][C:30]([NH2:31])=[CH:29][CH:28]=1)=[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:31][C:30]3[CH:32]=[CH:33][C:27]([C:25]([O:24][CH2:22][CH3:23])=[O:26])=[CH:28][CH:29]=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 2337BenzocaineHCID 67885997trans-9-bromo-5-carboxymethyl-6-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 131719949trans-9-Bromo-5-(p-ethoxycarbonylphenylcarbamoylmethyl)-6-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 82.8%

Procedure

A procedure similar to that described in Example 52 was carried out with trans-9-bromo-5-carboxymethyl-6-methyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (50 mg, 0.14 mmol) and p-ethoxycarbonylaniline (24 mg, 0.15 mmol) to give 58 mg of the title compound (82%): mp 282°~292° C.; 1H NMR (270 MHz, DMSO-d6) δ12.09 (s, 1H), 10.33 (s, 1H), 7.90 (d, 2H, J=8.6 Hz), 7.70 (d, 2H, J=8.6 Hz), 7.21 (s, 1H), 7.18 (s, 1H), 4.92~5.02 (m, 1H), 4.28 (q, 2H, J =6.9 Hz), 3.20 (dd, 1H, J=17.8, 5.9 Hz), 2.52~2.66 (m, 3H), 2.28~2.42 (m, 1H), 1.32 (t, 3H, J=6.9 Hz), 0.87 (d, 3H, J=6.9 Hz).

Sources & evidence

ORD record
ord-e4dd73a88daa4b1c91a553366878003f
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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