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US 2024/0254081 A1Published application
Catalytic tryptamine processes and precursors
AssigneeKare Chemical Technologies Inc.
InventorsKamaluddin ABDUR-RASHID, Kareem ABDUR-RASHID, Wenli JIA
Life of this patent
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Abstract
The present disclosure relates to the use of tryptamine precursor compounds and zinc amide enolate compounds for the preparation of tryptamines. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of tryptamines using the zinc amide enolate compounds and the tryptamine precursor compounds.
Claims22
A process for the preparation of compounds of Formula (III):
- comprising contacting a compound of Formula (I):
- with a compound of Formula (II):
- in the presence of a catalyst,
- wherein,
- R1 is hydrogen, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C20)-cycloalkyl, (C6-C20)-aryl, (C5-C20)-heteroaryl, —C(═O)—(C1-C20)-alkyl, —(C═O)—O—(C1-C20)-alkyl, ORc, or NRc2, each of which are optionally substituted with halogen, OH, optionally substituted phenyl or (C1-C6)-alkyl, and wherein Rc is hydrogen, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C20)-cycloalkyl, or (C6-C20)-aryl, and one or more of the carbon atoms in the alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl or acyl groups of R1 is optionally replaced with a heteroatom selected from the group consisting of O, S, N, P and Si, which, where possible, is optionally substituted with one or more groups selected from halo, OH, optionally substituted phenyl or (C1-C6)-alkyl;
- R2 to R10 represent hydrogen, deuterium, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C20)-cycloalkyl, (C6-C20)-aryl, (C5-C20)-heteroaryl, —C(═O)—(C1-C20)-alkyl, or two adjacent or geminal groups are bonded together to form an optionally substituted ring, each of which is optionally substituted with halogen, OH, or (C1-C6)-alkyl, and one or more of the carbon atoms in the alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl or acyl groups of R2 to R10 is optionally replaced with a heteroatom selected from the group consisting of O, S, N, P and Si, which is optionally substituted with one or more groups selected from halogen, OH, and (C1-C6)-alkyl;
- LG represents any suitable leaving group.
4 more elements
(canceled)
A Compound of Formula (V), Formula (VI), Formula (VII) or Formula (VIII):
- wherein,
- R1 represents hydrogen, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C20)-cycloalkyl, (C6-C20)-aryl, (C5-C20)-heteroaryl, —C(═O)—(C1-C20)-alkyl, —(C═O)—O—(C1-C20)-alkyl, ORc, or NRc2, each of which are optionally substituted with halogen, OH, optionally substituted phenyl or (C1-C6)-alkyl, and wherein Rc is hydrogen, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C20)-cycloalkyl, or (C6-C20)-aryl;
- R2 to R10 represent hydrogen, deuterium, (C1-C20)-alkyl, (C2-C20)-alkenyl, (C2-C20)-alkynyl, (C3-C20)-cycloalkyl, (C6-C20)-aryl, (C5-C20)-heteroaryl, —C(═O)—(C1-C20)-alkyl, or two adjacent or geminal groups are bonded together to form an optionally substituted ring, each of which is optionally substituted with halogen, OH, or (C1-C6)-alkyl, and one or more of the carbon atoms in the alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl or acyl groups of R2 to R10 is optionally replaced with a heteroatom selected from the group consisting of O, S, N, P and Si, which is optionally substituted with one or more groups selected from halogen, OH, and (C1-C6)-alkyl.
-26. (canceled)
Dependencies are inferred from the claim text.