Method for producing dicarboxylic acid compound
AssigneeDaiichi Sankyo Company, Limited
InventorsMasayuki Murakami, Yuichi Aki, Daisuke Fukatsu, Kenichi Kimura, Makoto Michida, Koji Hamaoka
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Abstract
It is an object of the present invention to provide an excellent method for producing an excellent therapeutic agent. The solution of the present invention is as shown in the following scheme: wherein R1 represents a C1-C6 alkyl group, R2 represents a C1-C6 alkyl group, and R3 represents a C1-C6 alkyl group.
Claims15
A method for producing a compound represented by formula (13) or a pharmacologically acceptable salt thereof, the method comprising:
- (i) a step of
- 1) reacting a compound represented by formula (10) or a compound represented by formula (11) with 3-(chlorosulfonyl)benzoyl chloride in a solvent to obtain a condensate, and then
- 2) reacting the condensate with a compound represented by formula (3) in a solvent in the presence of a base to produce a compound represented by formula (12):
- wherein R1 represents a C1-C6 alkyl group, R2 represents a C1-C6 alkyl group, R3 represents a C1-C6 alkyl group, and HX represents an acid;
- and
- (ii) a step of subjecting the compound represented by formula (12) produced in the previous step to a hydrolysis reaction in the presence of aqueous alkali in a solvent to produce a compound represented by formula (13):
- wherein R1 represents a C1-C6 alkyl group, R2 represents a C1-C6 alkyl group, and R3 represents a C1-C6 alkyl group.
A method for producing a compound represented by formula (10) or a compound represented by formula (11), the method comprising:
- (i) a step of subjecting a compound represented by formula (6) to a condensation reaction with 5-chloro-2-nitrobenzoyl chloride in a solvent in the presence of a base to produce a compound represented by formula (8):
- wherein R3 represents a C1-C6 alkyl group;
- (ii) a step of reacting the compound represented by formula (8) produced in the previous step with piperidine in a solvent to produce a compound represented by formula (9):
- wherein R3 represents a C1-C6 alkyl group;
- and
- (iii) a step of treating the compound represented by formula (9) produced in the previous step with an acid in a solvent in the presence of a catalyst under a hydrogen atmosphere to produce a compound represented by formula (10);
- or a step of treating the compound represented by formula (9) produced in the previous step in a solvent in the presence of a catalyst under a hydrogen atmosphere to produce a compound represented by formula (11):
- wherein R3 represents a C1-C6 alkyl group.
A method for producing a compound represented by formula (6), the method comprising:
- (i) a step of reacting a compound represented by formula (4) with 1-methyl-4-nitrobenzene in a solvent in the presence of C1-C6 alkyl formate and a base to produce a compound represented by formula (5):
- wherein R3 represents a C1-C6 alkyl group;
- and
- (ii) a step of treating the compound represented by formula (5) produced in the previous step in a solvent in the presence of a hydrogenation catalyst and a catalyst poison under a hydrogen atmosphere to produce a compound represented by formula (6):
- wherein R3 represents a C1-C6 alkyl group.
A method for producing a compound represented by formula (3), the method comprising:
- (i) a step of treating a compound represented by formula (1) in a solvent in the presence of C1-C6 alkylamine and a palladium catalyst under a hydrogen atmosphere to obtain a compound represented by formula (2);
- and
- (ii) a step of heating and treating the compound represented by formula (2) produced in the previous step in a solvent in the presence of hydrogen chloride to obtain a compound represented by formula (3):
- wherein R1 represents a C1-C6 alkyl group and R2 represents a C1-C6 alkyl group.
Dependencies are inferred from the claim text.