Process for producing amine derivatives
AssigneeTakeda Chemical Industries, Ltd.
InventorsMakoto Yamashita, Kaneyoshi Kato, Hiroyuki Tawada
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Abstract
This invention provides a convenient and industrially advantageous process producing amine derivatives having the action of inhibiting the secretion and accumulation of amyloid β protein. In Compound (I), the ether linkage is selectively cleaved without cleaving the amide linkage present in the same molecule and tertiary amines are not converted into quaternary salts, and thus Amine Derivative (V) with good qualities having the action of inhibiting the secretion and accumulation of amyloid β protein can be obtained in high yield.
Claims10
A process for producing a compound represented by the formula:
- wherein R1 and R2 each represent a hydrogen atom or an optionally substituted C1-6 alkyl group, or may, together with their adjacent nitrogen atom, form an optionally substituted nitrogen-containing heterocyclic ring, ring A represents an optionally substituted benzene ring, ring B represents an optionally substituted 4- to 8-membered ring, and Y represents an optionally substituted divalent C1-6 aliphatic hydrocarbon group, or a salt thereof, comprising selectively cleaving the ether linkage of a compound represented by the formula:
- wherein R represents an optionally substituted hydrocarbon group and the other symbols have the same meanings as defined above, or a salt thereof wherein the ether linkage is selectively cleaved in the presence of an acid and mercaptan or sulfide.
A process for producing a compound represented by the formula:
- wherein R1 and R2 each represent a hydrogen atom or an optionally substituted C1-6 alkyl group, or may, together with their adjacent nitrogen atom, form an optionally substituted nitrogen-containing heterocyclic ring, ring A represents an optionally substituted benzene ring, ring B represents an optionally substituted 4- to 8-membered ring, X represents an optionally substituted hydrocarbon group or an optionally substituted cyclic group, and Y represents an optionally substituted divalent C1-6 aliphatic hydrocarbon group, or a salt thereof, comprising selectively cleaving the ether linkage of a compound represented by the formula:
- wherein R represents an optionally substituted hydrocarbon group and the other symbols have the same meanings as defined above, or a salt thereof to produce a compound represented by the formula:
- wherein the symbols have the same meanings as defined above, or a salt thereof, then reacting the same with a compound represented by the formula:
- X—L
- wherein X has the same meaning as defined above and L represents an leaving group or a hydroxyl group, to produce a compound represented by the formula
- wherein the symbols have the same meanings as defined above, or a salt thereof wherein the ether linkage is selectively cleaved in the presence of an acid and mercaptan or sulfide, and then subjecting the same to reduction reaction.
A process for producing a compound represented by the formula:
- wherein R1 and R2 each represent a hydrogen atom or an optionally substituted C1-6 alkyl group, or may, together with their adjacent nitrogen atom, form an optionally substituted nitrogen-containing heterocyclic ring, ring A represents an optionally substituted benzene ring, ring B represents an optionally substituted 4- to 8-membered ring, X represents an optionally substituted hydrocarbon group or an optionally substituted cyclic group, and Y represents an optionally substituted divalent C1-6 aliphatic hydrocarbon group, or a salt thereof, comprising allowing a compound represented by the formula:
- wherein the symbols have the same meanings as defined above, or a salt thereof to react with a compound represented by the formula:
- X—L
- wherein X has the same meaning as defined above and L represents an leaving group or a hydroxyl group, to produce a compound represented by the formula:
- wherein the symbols have the same meanings as defined above, or a salt thereof, and then subjecting the same to reduction reaction.
Dependencies are inferred from the claim text.