tert-butyl N-[(4-aminophenyl)methyl]carbamate → 9-Bromo-5-[(p-tert-butoxycarbonylaminomethylphenyl)carbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52552Notes

Reaction equation

HRID 52552 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.[C:21]([O:25][C:26]([NH:28][CH2:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:34][C:33]3[CH:35]=[CH:36][C:30]([CH2:29][NH:28][C:26]([O:25][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:27])=[CH:31][CH:32]=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 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 539471179-Bromo-5-[(p-tert-butoxycarbonylaminomethylphenyl)carbamoylmethyl]-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 96.2%

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 p-tert-butoxycarbonylaminomethylaniline (130 mg, 0.5 mmol) to give 230 mg of the title compound (80%): mp 156°~157° C.; 1H NMR (270 MHz, DMSO-d6) δ12.06 (s, 1H), 9.98 (s, 1H), 7.48 (d, 2H, J=8.6 Hz), 7.34 (t, 1H, J=5,7 Hz), 7.24 (bs, 1H), 7.17 (bs, 1H), 7.15 (d, 2H, J=8.6 Hz), 5.16~5.26 (m, 1H), 4.06 (d, 2H, J=5.7 Hz), 3.06 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1 Hz), 2.56~2.65 (m, 2H), 2.10 (dm, 1H, J=13.5 Hz), 1.81~1.96 (m, 1H), 1.39 (s, 9H).

Sources & evidence

ORD record
ord-7e3ce657ffea4a2b8dddde4d7cfcd952
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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