Triethylamine → N-[(1R)-1-(3-Bromophenyl)ethyl]-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2-methoxyphenyl}urea

HRID 1817439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1817439
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[C:18]([O:23][CH3:24])[CH:17]=1.C(N(CC)CC)C.ClC(Cl)(O[C:36](=[O:42])OC(Cl)(Cl)Cl)Cl.[Br:44][C:45]1[CH:46]=[C:47]([C@H:51]([NH2:53])[CH3:52])[CH:48]=[CH:49][CH:50]=1>C(Cl)(Cl)Cl>[Br:44][C:45]1[CH:46]=[C:47]([C@H:51]([NH:53][C:36]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:17][C:18]=2[O:23][CH3:24])=[O:42])[CH3:52])[CH:48]=[CH:49][CH:50]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 218910314-((6,7-Dimethoxyquinolin-4-yl)oxy)-2-methoxyanilineHCID 22831503(R)-1-(3-bromophenyl)ethanamine

Produkt 1

HCID 57881594N-[(1R)-1-(3-Bromophenyl)ethyl]-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-2-methoxyphenyl}ureaAusbeute 17,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel3×

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-methoxyaniline (91 mg) was dissolved in chloroform (2 ml) and triethylamine (0.2 ml) to prepare a solution. A solution of triphosgene (70 mg) in chloroform (0.4 ml) was then added to the solution, and the mixture was stirred at room temperature for one hr. Next, a solution of (1R)-1-(3-bromophenyl)ethylamine (70 mg) in chloroform (0.4 ml) was added thereto, and the mixture was stirred at room temperature for 10 hr. The stirred mixture was purified by chromatography on silica gel using chloroform/methanol for development to give the title compound (23 mg, yield 15%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 10 hr
  2. customThe stirred mixture was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-750b224c4f0e42bd9fd53432fddc1762
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598258B2

Notizen zur Reaktion

Wird geladen…