Development of a Scalable Synthetic Route to GSK369796 ( N-tert -Butyl Isoquine), a Novel 4-Aminoquinoline Antimalarial Drug

  • Lawrence R
  • Dennis K
  • O’Neill P
 et al. 
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Abstract

An improved process to the 4-aminoquinoline antimalarial GSK369796 is described. Although the initial synthetic route consisted of only two steps from readily available starting materials, the product isolated via the key Mannich reaction was hampered by both low yields and low purity. In addn. to instability under the reaction conditions used for the Mannich reaction, the drug substance was found to decomp. during attempts to purify by recrystn. Reaction conditions were developed that resolved these issues, culminating in the successful prodn. of multi-kg quantities of GSK369796 in >98% a/a purity and in 57% overall yield. [on SciFinder(R)]

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Authors

  • Ron M Lawrence

  • Katherine C Dennis

  • Paul M. O’Neill

  • Dirk Uwe Hahn

  • Michael Roeder

  • Cornelia Struppe

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