Atrolactic acid → 2-(6-Nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxaline-9-ylcarbamoyl)ethyl-(4-hydroxy)benzene

HRID 863503

Reaktionsgleichung

Reaktionsgleichung von HRID 863503
O[C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])C(O)=O.[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].[NH2:25][CH:26]1[CH2:44][C:30]2[C:31]3[NH:32][C:33](=[O:43])[C:34](=[O:42])[NH:35][C:36]=3[CH:37]=[C:38]([N+:39]([O-:41])=[O:40])[C:29]=2[CH2:28][CH2:27]1.C(N(CC)CC)C.[O:52]1CCCC1>>[N+:39]([C:38]1[C:29]2[CH2:28][CH2:27][CH:26]([NH:25][C:13]([CH2:6][CH2:2][C:7]3[CH:8]=[CH:9][C:10]([OH:52])=[CH:11][CH:12]=3)=[O:14])[CH2:44][C:30]=2[C:31]2[NH:32][C:33](=[O:43])[C:34](=[O:42])[NH:35][C:36]=2[CH:37]=1)([O-:41])=[O:40]

Komponenten

6

Edukt 5

HCID 1303Atrolactic acidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 196962049-Amino-6-nitro-1,4,7,8,9,10-hexahydro-benzo[f]quinoxaline-2,3-dione

Produkt 1

HCID 196961482-(6-Nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxaline-9-ylcarbamoyl)ethyl-(4-hydroxy)benzene

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Hydroxyphenylpropionic acid (0.17 g, 1 mmol) and carbonyldiimidazole (0.16 g, 1 mmol) in 5 mL tetrahydrofuran were stirred at reflux for 15 min. The mixture was added to the starting amine (example 15, 0.15 g, 0.5 mmol) and heated at 60° C. for 30 min. Triethylamine (0.1 g) was added and the mixture heated an additional 5 h. The solvent was removed by rotoevaporation, and the residue suspended in tetrahydrofuran. The solid was collected by filtration and dried. CI MS m/e (M+1) 425. H-NMR (400 MHz, dmso) 1H, s, 12.1; 1H, s, 11.45; 5 Ar H, 8.0-6.6 including 1H, s, 7.65; 1H, m, 4.1; +other ring protons.

Aufarbeitung

  1. temperatureat reflux for 15 min
  2. temperaturethe mixture heated an additional 5 h
  3. customThe solvent was removed by rotoevaporation
  4. filtrationThe solid was collected by filtration
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d3fc66527be948aeb22bf31150c635e9
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05721234

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