Reaktion #1904601

ord-4d90ca0289bc44f4a1b66085e4474101

Reaktionsgleichung

CC[C@H](N)c1ccccc1
(1S)-1-phenylpropylamine
CCN(CC)CC
triethylamine
COc1cc2nccc(Oc3ccc(N)cc3)c2cc1OC
4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline
O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl
triphosgene
CC[C@H](NC(=O)Nc1ccc(Oc2ccnc3cc(OC)c(OC)cc23)cc1)c1ccccc1
title compound
Ausbeute 121.9%
CC[C@H](NC(=O)Nc1ccc(Oc2ccnc3cc(OC)c(OC)cc23)cc1)c1ccccc1
N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N′-[(1S)-1-phenylpropyl]urea
Ausbeute 121.9%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGthe mixture was stirred at room temperature for 10 hr
  2. 2
    SonstigeThe stirred mixture was purified by chromatography on silica gel

Vorschrift

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (70 mg) was dissolved in chloroform (1 ml) and triethylamine (0.1 ml) to prepare a solution. A solution of triphosgene (33 mg) in chloroform (0.2 ml) was then added to the solution, and the mixture was stirred at room temperature for 75 min. Next, a solution of (1S)-1-phenylpropylamine (31 mg) in chloroform (0.2 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 (62 mg, yield 57%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07598258B2uspto-grants-2009_10