4-Aminobenzonitrile → HCID 44285544, compound

HRID 52526Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([OH:20])=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[C:21]([C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)#[N:22]>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:20])[NH:27][C:26]3[CH:28]=[CH:29][C:23]([C:21]#[N:22])=[CH:24][CH:25]=3)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 104723389-bromo-5-carboxymethyl-6,7-dihydro-1H, 5 H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 44285544HCID 44285544, compoundYield 41%

Procedure

A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (170 mg, 0.5 mmol) and p-cyanoaniline (60 mg, 0.51 mmol) to give 90 mg of the title compound (41%): mp>270° C.; 1H NMR (270 MHz, DMSO-d6) δ12.06 (s, 1H), 10.44 (s, 1H), 7.77 (d, 2H, J=9.2 Hz), 7.74 (d, 2H, J=9.2 Hz), 7.23 (bs, 1H), 7.17 (bs, 1H), 5.18~5.26 (m, 1H), 3.03 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.83 (dm, 1H, J=17.1Hz), 2.65(d, 2H, J=7.6Hz),2.11 (dm, 1H, J=13.5Hz), 1.83~1.96 (m, 1H).

Sources & evidence

ORD record: ord-815d97a031e242a9be1ce14fc45bff07
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616586

Reaction notes

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