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Patent Application
App. No. 14/592,568

PROCESS FOR PRODUCING V-COELENTERAZINE COMPOUNDS

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Quick Facts
Patent No.
US None
App. No.
14/592,568
Abstract

A simple process for producing ν-coelenterazine compounds has been desired. The invention provides a process for producing a ν-coelenterazine compound represented by general formula (II) which comprises (1) the step of reacting a compound represented by general formula (VIII) with a methyltriphenylphosphonium salt in the presence of a base to give a compound represented by general formula (IX), (2) the step of performing a ring-closing metathesis reaction on any one selected from the group consisting of the compound represented by general formula (IX) and a compound represented by general formula (X) which is the compound represented by general formula (IX) wherein the amino is protected with R 5 , and then deprotecting R 4 and, if any, R 5 to give a ν-coelenteramine compound represented by general formula (XIV), and (3) the step of reacting the compound represented by general formula (XIV) with a compound represented by general formula (XV) to give the compound represented by general formula (II).

Claims (9)

1 - 13 . (canceled)

14 . The method for producing a compound represented by formula (VIII):

wherein R 1 is hydrogen, a halogen, a substituted or unsubstituted hydrocarbon group, or a substituted or unsubstituted heterocyclic group, and R 4 is a protecting group,

which comprises: (1) reacting 2-amino-3,5-diburomo-6-chloropyrazine with R 1 MgX and ZnCl 2 , wherein R 1 is the same as defined above and X is a halogen, in the presence of a palladium catalyst to give a compound represented by formula (V):

wherein R 1 is the same as defined above,

(2) reacting the compound represented by formula (V) with a compound represented by formula (VI):

wherein R 4 is the same as defined above, in the presence of a palladium catalyst and a base to give a compound represented by formula (VII):

wherein R 1 and R 4 are the same as defined above, and,

(3) reacting the compound represented by formula (VII) with tributyl(vinyl)tin in the presence of a palladium catalyst to give the compound represented by formula (VIII).