CA2190851A1 - Palladium catalyzed ring closure of triazolyl tryptamine - Google Patents

Palladium catalyzed ring closure of triazolyl tryptamine

Info

Publication number
CA2190851A1
CA2190851A1 CA002190851A CA2190851A CA2190851A1 CA 2190851 A1 CA2190851 A1 CA 2190851A1 CA 002190851 A CA002190851 A CA 002190851A CA 2190851 A CA2190851 A CA 2190851A CA 2190851 A1 CA2190851 A1 CA 2190851A1
Authority
CA
Canada
Prior art keywords
ring closure
tryptamine
triazolyl
catalyzed ring
palladium catalyzed
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002190851A
Other languages
French (fr)
Other versions
CA2190851C (en
Inventor
Cheng Y. Chen
Robert D. Larsen
Thomas R. Verhoeven
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Sharp and Dohme LLC
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US08/248,288 external-priority patent/US5567824A/en
Application filed by Individual filed Critical Individual
Publication of CA2190851A1 publication Critical patent/CA2190851A1/en
Application granted granted Critical
Publication of CA2190851C publication Critical patent/CA2190851C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A new process is described for the synthesis of the triazolyl tryptamine (.alpha.) and related compounds. The process involves a palladium-catalyzed ring closure between a substituted ortho-iodoaniline and a protected 1-alkynol. The process is carried out at high temperature, e.g. 100 ~C, in a dry inert solvent, e.g., DMF and in the presence of a proton acceptor, e.g., Na2CO3 or a trialkylamine. The triazolyl tryptamine, as well as acid addition salts thereof, is a 5 HT1D receptor agonist having anti-migraine properties.
CA002190851A 1994-05-24 1995-05-19 Palladium catalyzed ring closure of triazolyl tryptamine Expired - Fee Related CA2190851C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US248,288 1994-05-24
US08/248,288 US5567824A (en) 1994-05-24 1994-05-24 Palladium catalyzed ring closure of triazolyltryptamine
PCT/US1995/005506 WO1995032197A1 (en) 1994-05-24 1995-05-19 Palladium catalyzed ring closure of triazolyl tryptamine

Publications (2)

Publication Number Publication Date
CA2190851A1 true CA2190851A1 (en) 1995-11-30
CA2190851C CA2190851C (en) 2006-12-12

Family

ID=26789628

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002190851A Expired - Fee Related CA2190851C (en) 1994-05-24 1995-05-19 Palladium catalyzed ring closure of triazolyl tryptamine

Country Status (2)

Country Link
CA (1) CA2190851C (en)
CZ (1) CZ296249B6 (en)

Also Published As

Publication number Publication date
CZ296249B6 (en) 2006-02-15
CA2190851C (en) 2006-12-12
CZ343596A3 (en) 1997-07-16

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Legal Events

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MKLA Lapsed

Effective date: 20130521