(2S,3R)-N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide, novel salt forms, and methods of use thereof
The present invention relates to (2S,3R)-N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide, novel salt forms thereof, methods for its preparation, novel intermediates, and methods for treating a wide variety of conditions and disorders, including those associated with dysfunction of the central and autonomic nervous systems.
1. A method of manufacturing stereoisomerically enriched (2S,3R)-N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3yl)benzofuran-2-carboxamide or a pharmaceutically acceptable salt thereof comprising sequential dynamic resolution and stereoselective reductive amination of 2-((3pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-one.
2. A method of manufacturing stereoisomerically enriched (2S,3R)-N-(2-((3-pyridinyl)methyl)-1 -azabicyclo[2.2.2]oct-3yl)benzofuran-2-carboxamide or a pharmaceutically acceptable salt thereof comprising a reaction using stereoisomerically enriched (2S,3R)-2-((3-pyridinyl)methyl)-3-amino-1-azabicyclo [2.2.2]octane.
3. Stereoisomerically enriched (2S,3R)-2-((3-pyridinyl)methyl)-3-amino-1-azabicyclo[2.2.2]octane.
4. Stereoisomerically enriched (2S)-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-one di-p-toluoyl-D-tartrate.