title: Synthesis of 3H, 13C,2H3,15N and 14C-labelled SCH 466036, a histamine 3 receptor antagonist.
abstract: The synthesis of [(3)H]SCH 466036, [Me-(3)H3]SCH 466036, [(13)C,(2)H3,(15)N]SCH 466036 and [(14)C]SCH 466036 is described. [(3)H]SCH 466036 was prepared in two steps via Raney Ni-catalysed exchange with tritiated water. [Me-(3)H3]SCH 466036 was prepared in a single step from [(3)H]methyl iodide in 45% yield. [(13)C,(2)H3,(15)N]SCH 466036 was prepared in two steps from [(15)N]hydroxylamine and [(13)C,(2)H3]methyl iodide with an overall yield of 16%. [(14)C]SCH 466036 was prepared in seven steps from [(14)C]potassium cyanide in an overall yield of 13%.
authors.affiliation: Merck Research laboratories, Labeled Compound Synthesis, Department of Process Chemistry, 126 E. Lincoln Avenue, RY 80R, Rahway, NJ, 07065, USA.
authors.forename: D
authors.initials: D
authors.lastname: Hesk
authors.forename: S
authors.initials: S
authors.lastname: Borges
authors.forename: R
authors.initials: R
authors.lastname: Dumpit
authors.forename: S
authors.initials: S
authors.lastname: Hendershot
authors.forename: D
authors.initials: D
authors.lastname: Koharski
authors.forename: C
authors.initials: C
authors.lastname: Lavey
authors.forename: P
authors.initials: P
authors.lastname: McNamara
authors.forename: K
authors.initials: K
authors.lastname: Voronin
mesh_terms: D000631:Aminopyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D002250:Carbon Radioisotopes / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry; D054828:Histamine H3 Antagonists / Q000138:chemical synthesis*; D009587:Nitrogen Isotopes / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*; D014316:Tritium / Q000737:chemistry
chemical_list: C000602385:(1-((2-aminopyridin-4-yl)methyl)piperidin-4-yl)(4-((methoxyimino)(pyridin-2-yl)methyl)piperidin-1-yl)methanone; D000631:Aminopyridines; D002250:Carbon Radioisotopes; D054828:Histamine H3 Antagonists; D009587:Nitrogen Isotopes; D010880:Piperidines; D019275:Radiopharmaceuticals; D014316:Tritium; D003903:Deuterium
keywords: H3 antagonist; SCH 466036; carbon-14; deuterium; nitrogen-15; tritium