764714-59-2Relevant articles and documents
Synthesis of a bicyclic piperazine from l-aspartic acid and application of a fluoride-promoted SNAr coupling
Sieser, Janice E.,Singer, Robert A.,McKinley, Jason D.,Bourassa, Dennis E.,Teixeira, John J.,Long, James
, p. 1328 - 1335 (2012/01/12)
The process development is reported of a pivotal C-N bond formation involving ((7R,9aS)-octahydro-1H-pyrido[1,2-a]pyrazin-7-yl)methanol (2) undergoing nucleophilic aromatic substitution with 3-chlorobenzo[d]isoxazole (3) to furnish ((7R,9aS)-2-(benzo[d]isoxazol-3-yl)octahydro-1H-pyrido[1,2-a] pyrazin-7-yl)methanol (4) as a key intermediate for a family of compounds (1). Essential to the success of the coupling is the use of fluoride in combination with a phase transfer catalyst. The development of an alternative route to bicyclic piperazine 2 that uses l-aspartic acid (20) as a starting material to avoid the need for a classical salt resolution is described.
New entries in Lewis acid-Lewis base bifunctional asymmetric catalyst: Catalytic enantioselective Reissert reaction of pyridine derivatives
Ichikawa, Eiko,Suzuki, Masato,Yabu, Kazuo,Albert, Matthias,Kanai, Motomu,Shibasaki, Masakatsu
, p. 11808 - 11809 (2007/10/03)
The first catalytic enantioselective Reissert reaction of pyridine derivatives that affords products with excellent regio- and enantioselectivity is described. The key for success is the development of new Lewis acid-Lewis base bifunctional asymmetric catalysts containing an aluminum as a Lewis acid and sulfoxides or phosphine sulfides as a Lewis base. These reactions are useful for the synthesis of a variety of chiral piperidine subunits, and catalytic enantioselective formal synthesis of CP-293,019, a selective D4 receptor antagonist, was achieved. Preliminary mechanistic studies indicated that both sulfoxides and phosphine sulfides can activate TMSCN as a Lewis base. In addition, the sulfoxides with appropriate stereochemistry might stabilize a highly enantioselective bimetallic complex (a presumed active catalyst) through internal coordination to aluminum. Copyright
Synthesis, SAR and pharmacology of CP-293,019: A potent, selective dopamine D4 receptor antagonist
Sanner, Mark A.,Chappie, Thomas A.,Dunaiskis, Audrey R.,Fliri, Anton F.,Desai, Kishor A.,Zorn, Stevin H.,Jackson, Elisa R.,Johnson, Celeste G.,Morrone, Jean M.,Seymour, Patricia A.,Majchrzak, Mark J.,Faraci, W. Stephen,Collins, Judith L.,Duignan, David B.,Di Prete, Cecilia C.,Lee, Jae S.,Trozzi, Angela
, p. 725 - 730 (2007/10/03)
A series of novel, potent and selective pyrido[1,2-a]pyrazine dopamine D4 receptor antagonists are reported including CP-293,019 (D4 K(i) = 3.4 nM, D2 K(i) > 3,310 nM), which also inhibits apomorphine-induced hyperlocomotion in rats after oral dosing.
