title: Solid-phase preparation of a pilot library derived from the 2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-amine scaffold.
abstract: A convenient and reliable solid-phase strategy for the synthesis of di- and trisubstituted benzazepine derivatives was developed. 5-Amino-1-tert-butoxycarbonyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine and 5-amino-1-tert-butoxycarbonyl-7-bromo-2,3,4,5-tetrahydro-1H-benzo[b]azepine G-protein coupled receptor-targeted (GPCR-targeted) scaffolds were efficiently synthesized in a six-step solution-phase process, immobilized on the acid-labile FMPB-AM resin, and further functionalized through acylation, sulfonation, reductive amination, alkylation, and Suzuki or Buchwald-Hartwig cross-coupling reactions. The efficacy of this strategy was exemplified by the preparation of an original pilot library of di- and trisubstituted benzazepines obtained in high purity as assessed by both 1H NMR and liquid chromatography/mass spectrometry (LC/MS) analysis.
authors.affiliation: Département de Pharmacochimie de la Communication Cellulaire, Institut Gilbert Laustriat, LC1-UMR CNRS/ULP 7175, Faculté de Pharmacie de Strasbourg, 74 route du Rhin BP24, 67401 Illkirch, Cedex, France.
authors.forename: Damien
authors.initials: D
authors.lastname: Boeglin
authors.forename: Dominique
authors.initials: D
authors.lastname: Bonnet
authors.forename: Marcel
authors.initials: M
authors.lastname: Hibert
mesh_terms: D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001552:Benzazepines