Benzylamine → HCID 19963232, compound

HRID 52476Notes

Reaction equation

HRID 52476 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([CH2:16][C:17]([OH:19])=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([CH2:16][C:17](=[O:19])[NH:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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 100191838-bromo-5-carboxymethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 19963232HCID 19963232, compoundYield 51%

Procedure

A procedure similar to that described in Example 5 was carried out with 8-bromo-5-carboxymethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione (130 mg, 0.40 mmol) and benzylamine (48 μL, 0.44 mmol) to give 82 mg of the title compound (51%): mp 252° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.13 (s, 1H), 8.69 (t, 1H, J=6 Hz), 7.18~7.34 (m, 5H), 7.20 (s, 2H), 5.16~5.22 (m, 1H), 4.27 (d, 2H, J=6 Hz), 2.80 (dm, 1H, J=18 Hz), 2.55 (dm, 1H, J=14 Hz), 2.46 (m, 1H, J=14 Hz), 1.87~2.03 (m, 1H).

Sources & evidence

ORD record
ord-8a16d53701b64d418c8bbe88b7a12665
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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