US 2004/0204587 A1 · Process for the synthesis of 3-cyano-6-alkoxy-7-nitro-4-quinolones

Abstract

There is provided a process for the preparation of 3-cyano-6-alkoxy-7-nitro-4-quinolone intermediates useful for the preparation of protein tyrosine kinase (PTK) inhibitors which are useful in the treatment of cancer of the formula: 1 wherein R is alkyl(C1-C3) prepared by reacting a substituted anthranilate with N,N-dimethylformamide dimethyacetal to obtain a N,N-dimethylamidine which is condensed with t-butylcyanoacetate to obtain a N-(2-cyano-2-t-butoxycarbonylvinyl)anthranilate, which is hydrolyzed to yield a N-(2-cyano-2-carboxyvinyl)anthranilate followed by decarboxylating to obtain a N-(2-cyano-2-carboxyvinyl)anthranilate followed by cyclizing to obtain a 3-cyano-6-alkoxy-7-nitro-4-quinolone.

Claims34

Dependent claims

A process for the production of a 3-cyano-6-alkoxy-7-nitro-4-quinolone comprising:

a) reacting a substituted anthranilate of formula (I) with dimethylformamide dimethyl acetal:
9
wherein R is an alkyl;
to obtain a compound of formula (II):
10
b) condensing the compound of formula (II) with t-butylcyanoacetate to obtain a compound of formula (III):
11
c) hydrolyzing the compound of formula (III) to yield compound of formula (IV):
12
d) decarboxylating the compound of formula (IV) to a compound of formula (V):
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e) cyclizing the compound of formula (V) to obtain a 3-cyano-6-alkoxy-7-nitro-4-quinolone of formula:
14

10 more elements

Dependencies are inferred from the claim text.

Process for the synthesis of 3-cyano-6-alkoxy-7-nitro-4-quinolones

Life of this patent

Process for the synthesis of 3-cyano-6-alkoxy-7-nitro-4-quinolones

Life of this patent

Abstract

Claims34