title: Addition of benzylic and allylic organozinc and Grignard reagents to resin-bound imines to provide alpha-branched secondary amines bearing a wide variety of functional groups. Utility in the synthesis of beta-3 adrenergic receptor agonists.
abstract: Benzylic and allylic organozinc and Grignard reagents have been added to resin-bound imines to provide alpha-branched secondary amines. Many functional groups, including electrophilic groups, were compatible with this methodology. Three modules--a resin-bound primary amine, an aromatic aldehyde, and the organometallic--were independently varied to produce a combinatorial library of alpha-branched secondary amines designed as beta-3 adrenergic receptor agonists.
authors.affiliation: Bristol-Myers Squibb Pharmaceutical Research Institute, P O Box 5400, Princeton, New Jersey 08543, USA.
authors.forename: Gang
authors.initials: G
authors.lastname: Wu
authors.forename: Zhen-Wei
authors.initials: ZW
authors.lastname: Cai
authors.forename: Mark S
authors.initials: MS
authors.lastname: Bednarz
authors.forename: Octavian R
authors.initials: OR
authors.lastname: Kocy
authors.forename: Ashvinikumar V
authors.initials: AV
authors.lastname: Gavai
authors.forename: Jollie D
authors.initials: JD
authors.lastname: Godfrey
authors.forename: William N
authors.initials: WN
authors.lastname: Washburn
authors.forename: Michael A
authors.initials: MA
authors.lastname: Poss
authors.forename: Philip M
authors.initials: PM
authors.lastname: Sher
mesh_terms: D058667:Adrenergic beta-3 Receptor Agonists; D000318:Adrenergic beta-Agonists / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D015032:Zinc / Q000737:chemistry*
chemical_list: D058667:Adrenergic beta-3 Receptor Agonists; D000318:Adrenergic beta-Agonists; D000588:Amines; D007097:Imines; D015032:Zinc; D001554:Benzene