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

HRID 1817435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1817435
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.ClC(Cl)(O[C:35](=[O:41])OC(Cl)(Cl)Cl)Cl.[Br:43][C:44]1[CH:45]=[C:46]([C@H:50]([NH2:52])[CH3:51])[CH:47]=[CH:48][CH:49]=1>C(Cl)(Cl)Cl>[Br:43][C:44]1[CH:45]=[C:46]([C@H:50]([NH:52][C:35]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([O:9][C:10]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]=[CH:12][CH:11]=3)=[CH:8][C:2]=2[Cl:1])=[O:41])[CH3:51])[CH:47]=[CH:48][CH:49]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroanilineHCID 22831503(R)-1-(3-bromophenyl)ethanamine

Produkt 1

HCID 57881602N-[(1R)-1-(3-Bromophenyl)ethyl]-N'-{2-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}ureaAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel3×

Versuchsvorschrift

2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (83 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 (64 mg, yield 46%).

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-578583e411fb457d9e3579323c17a651
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598258B2

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