High-purity quinoline derivative and method for manufacturing same
Provided is a compound represented by formula (IV) or a salt thereof, wherein the content of the compound represented by formula (I) is 350 ppm by mass or less.
1. A methanesulfonate salt of a compound represented by formula (IV), wherein the content of a compound represented by formula (A-1) is 60 ppm by mass or less
2. The methanesulfonate salt of a compound represented by formula (IV) according to claim 1 , wherein the content of a compound represented by formula (I) is 183 ppm by mass or less, and the content of a compound represented by formula (A-1) is 60 ppm by mass or less
3. A method for producing a compound represented by formula (IV)
or a salt thereof, comprising:
a step B of allowing a compound represented by formula (I)
or a salt thereof to react with a compound represented by formula (II-A) or formula (II-B)
wherein R 1 is a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 6-10 aryl group, or a C 7-11 aralkyl group, wherein the C 1-6 alkyl group or the C 2-6 alkenyl group may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom and a methoxy group, and wherein the C 6-10 aryl group or the C 7-11 aralkyl group may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom, a methyl group, a methoxy group, and a nitro group; and X is a halogen atom, in the presence of a base to thereby obtain a compound represented by formula (III)
wherein R 1 is the same group as above, and
a step C of, after allowing the compound represented by formula (III) obtained in the step B to react without isolation with cyclopropylamine, precipitating and isolating a compound represented by formula (IV)
or a salt thereof by introducing a hydrous organic solvent to a reaction solution.
4. The method according to claim 3 , comprising:
a step A of, after allowing a compound represented by formula (A-1)
to react with a compound represented by formula (A-2)
or a salt thereof in the presence of a base, precipitating and isolating a compound presented by formula (I)
or a salt thereof from a reaction solution by introducing a hydrous organic solvent to the reaction solution,
a step B of allowing the compound represented by formula (I)
or a salt thereof obtained in the step A to react with a compound represented by formula (II-A) or formula (II-B)
wherein R 1 is a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 6-10 aryl group, or a C 7-11 aralkyl group,
wherein the C 1-6 alkyl group or the C 2-6 alkenyl group may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom and a methoxy group, and wherein the C 6-10 aryl group or the C 7-11 aralkyl group may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom, a methyl group, a methoxy group, and a nitro group; and X is a halogen atom, in the presence of a base to thereby obtain a compound represented by formula (III)
wherein R 1 is the same group as above, and
a step C of, after allowing the compound represented by formula (III) obtained in the step B to react without isolation with cyclopropylamine, precipitating and isolating a compound represented by formula (IV)
or a salt thereof by introducing a hydrous organic solvent to a reaction solution.
5. The method according to claim 3 , further comprising a step D of converting the compound represented by formula (IV) obtained in the step C into a salt of the compound represented by formula (IV).
6. The method according to claim 5 , wherein the salt obtained in the step D is a methanesulfonate.
7. The method according to claim 3 , wherein the step B is a step of allowing the compound represented by formula (I)
or a salt thereof to react with the compound represented by formula (II-A)
wherein R 1 is a C 6-10 aryl group that may have one to three substituents that may be the same or different and are selected from the group consisting of a halogen atom, a methyl group, a methoxy group, and a nitro group; and X is a halogen atom,
in the presence of a base to thereby obtain a compound represented by formula (III)
wherein R 1 is the same group as above.
8. The method according to claim 3 , wherein the compound represented by formula (II-A) is phenyl chloroformate.
9. The methanesulfonate salt of a compound represented by formula (IV) according to claim 3 , wherein the content of the methanesulfonate salt of a compound represented by formula (IV) is 98.0% by mass or more
10. The methanesulfonate salt of a compound represented by formula (IV) according to claim 2 , wherein the content of the methanesulfonate salt of a compound represented by formula (IV) is 98.0% by mass or more
11. The methanesulfonate salt of a compound represented by formula (IV) according to claim 3 , wherein the content of the compound represented by formula (A-1) is determined by HPLC.
12. The methanesulfonate salt of a compound represented by formula (IV) according to claim 2 , wherein the content of the compound represented by formula (I) and the content of the compound represented by formula (A-1) are measured by HPLC.