- A straightforward mid high yielding synthesis of mefloquine - II
-
A new practical and high yielding synthesis of mefloquine (1) is described. Heteroarylation of 2-pyridylacetonitrile (2) gave the key intermediate 2-pyridyl-4-quinolylacetonitrile 4, which, on reaction with m-chloroperbenzoic acid, gave unexpectedly the cyanhydrine 5 The later, after base treatment afforded quantitatively the ketone 6.
- Adam, Solange
-
-
Read Online
- Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen
-
The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.
- Sterckx, Hans,De Houwer, Johan,Mensch, Carl,Herrebout, Wouter,Tehrani, Kourosch Abbaspour,Maes, Bert U.W.
-
p. 144 - 153
(2016/04/05)
-
- Use of (+)mefloquine for the treatment of malaria
-
Use of (+)-(11R,2′S)-α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol or a pharmaceutically acceptable salt thereof substantially free of its (?)-enantiomer in the manufacture of a medicament having reduced side-effect compared to the racemic (±)-(R*,S*)-α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol for treating or preventing malaria in a subject. A method of treating or preventing malaria with reduced side-effects comprising administration of (+)-(11R,2′S)-α-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol or a pharmaceutically acceptable salt thereof substantially free of its (?)-enantiomer.
- -
-
Page column 7-8
(2008/06/13)
-
- ONE POT SYNTHESIS OF [2, 8-BIS (TRIFLUOROMETHYL)-4- QUINOLINYL]2-PYRIDINYLMETHANONE, A MEFLOQUINE INTERMEDIATE
-
The present invention provides a simple single step process for the preparation of [2,8-bis (trifluoromethyl)-4-quinolinyl]-2 -pyridinylmethanone, comprising the step of condensing a halo-quinoline with an alpha-picolyl derivatives in the presence of a solvent, a base and a phase transfer catalyst at ?10° C. to +90° C.
- -
-
-