(S)-9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione → (S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(3-methoxycarbonylpropyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 862588Notes

Reaction equation

HRID 862588 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[C:12]([CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:24][C:25]1[CH:26]=[C:27]2[CH2:39][CH2:38][C@@H:37]([CH2:40][C:41](O)=[O:42])[N:29]3[C:30](=[O:36])[C:31](=[O:35])[NH:32][C:33]([CH:34]=1)=[C:28]23>>[Br:24][C:25]1[CH:26]=[C:27]2[CH2:39][CH2:38][C@@H:37]([CH2:40][C:41](=[O:42])[NH:14][C:13]3[CH:15]=[CH:16][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:11][C:12]=3[CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[N:29]3[C:30](=[O:36])[C:31](=[O:35])[NH:32][C:33]([CH:34]=1)=[C:28]23

Participants

3

Reactant 2

HCID 10088544(S)-9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneHCID 196983924-Tert-butoxycarbonylaminomethyl-2-(3-methoxycarbonylpropyl)aniline

Product 1

HCID 131720484(S)-9-Bromo-5-[p-tert-butoxycarbonylaminomethyl-o-(3-methoxycarbonylpropyl) phenylcarbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 62%

Procedure

A procedure similar to that described in Example 9-7) was performed with 4-tert-butoxycarbonylaminomethyl-2-(3-methoxycarbonylpropyl)aniline (130 mg, 0.4 mmol) and (S)-9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (136 mg, 0.4 mmol) to give 118 mg of the title compound (62%).

Sources & evidence

ORD record
ord-2c6f8629429a4b60a0ead062a7bed73d
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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