Benzoic Acid → 9-Bromo-5-benzoylaminomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52486Notes

Reaction equation

HRID 52486 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[CH2:17][CH2:16][CH:15]([CH2:18][NH2:19])[N:7]3[C:8](=[O:14])[C:9](=[O:13])[NH:10][C:11]([CH:12]=1)=[C:6]23.[C:20](O)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[Br:2][C:3]1[CH:4]=[C:5]2[CH2:17][CH2:16][CH:15]([CH2:18][NH:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:7]3[C:8](=[O:14])[C:9](=[O:13])[NH:10][C:11]([CH:12]=1)=[C:6]23

Participants

3

Reactant 2

HCID 243Benzoic AcidHCID 678861339-bromo-5-aminomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochloride

Product 1

HCID 104095219-Bromo-5-benzoylaminomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 59%

Procedure

A procedure similar to that described in Example 15 was carried out with 9-bromo-5-aminomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione hydrochloride (800 mg, 2.31 mmol) and benzoic acid (312 mg, 2.56 mmol) to give 564 mg of the title compound (59%): mp 169~175° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.03 (s, 1H), 8.66 (t, 1H, J=5.4 Hz), 7.77 (d, 2H, J=8.6 Hz), 7.41~7.56 (m, 3H), 7.24 (s, 1H), 7.19 (s, 1H), 5.03~5.13 (m, 1H), 3.62 (dt, 1H, J=11, 6.5 Hz), 3.28~3.40 (m, 1H), 3.10 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.78 (dm, 1H, J=17.1 Hz), 2.14 (dm, 1H, J=13.5 Hz), 1.73~1.89 (m, 1H).

Sources & evidence

ORD record
ord-c1077fdf7e5040638e3f9b359f043923
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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