Preparation of heteroarylcarboxamides
AssigneeAmerican Cyanamid Company
InventorsMarcus Knell, Monika Brink, Jan Hendrik Wevers, Willi Heinz
Life of this patent
Estimating the term…
Abstract
The invention relates to a process for the preparation of hetero)aryloxyheteroarylcarboxylic amide or ester of formula VI wherein A1, A2, A3, A4, A5 Hal, X, R1, and R4 are defined within, which process comprises preparing the heteroarylcarboxylic amide or ester of formula I or a salt thereof, from a trichoromethyl-heteroaromatic compound of formula II and reacting the compound of formula I with an aromatic or heteroaromatic hydroxyl compound of formula VII, R4—OH VII optionally in the presence of a base.
Claims12
A process for the preparation of a (hetero)aryloxyheteroarylcarboxylic amide or ester of formula VI
- wherein
- one of the groups A1, A2, A3, A4 and A1 represent a nitrogen atom and the other groups each independently represent CR3,
- Hal represents a halogen atom,
- X represents O or NR2,
- R1 represents an optionally substituted alkyl, aryl, heteroaryl or cycloalkyl group,
- R2 represents a hydrogen atom or an alkyl group, or
- R1 and R2 together with the interjacent ring form a heterocyclic group, and
- R3 each independently represent a hydrogen atom or an alkyl group, and R4 represents an optionally substituted aryl or heteroaryl group, which process comprises preparing the heteroarylcarboxylic amide or ester of formula I or a salt thereof,
- wherein Hal, A1 to A5, and R1 are as defined above, from a trichoromethyl-heteroaromatic compound of formula II
- and reacting the compound of formula I with an aromatic or heteroaromatic hydroxyl compound of formula VII,
- R4—OH VII
- wherein R4 is as hereinbefore defined, optionally in the presence of a base.
The compound of formula IA,
- wherein R1 represents an isopropyl group.
A process for the preparation of a (hetero)aryloxyheteroarylcarboxylic amide or ester of formula VI
- wherein
- one of the groups A1, A2, A3, A4 and A5 represent a nitrogen atom and the other groups each independently represent CR3,
- Hal represents a halogen atom,
- X represents NR2,
- R1 represents an optionally substituted alkyl, aryl, heteroaryl or cycloalkyl group,
- R2 represents a hydrogen atom or an alkyl group, or
- R1 and R2 together with the interjacent ring form a heterocyclic group, and
- R3 each independently represent a hydrogen atom or an alkyl group, and R4 represents an optionally substituted aryl or heteroaryl group, which process comprises preparing the heteroarylcarboxylic amide or ester of formula I or a salt thereof,
- wherein Hal, A1 to A5, and are as defined above and X is O or NR2, from a trichoromethyl-heteroaromatic compound of formula II
- and reacting the compound of formula I with an aromatic or hetemaromatic hydroxyl compound of formula VII,
- R4—OH VII
- wherein R4 is as hereinbefore defined, optionally in the presence of a base.
The compound of formula VIA
- wherein R4 represents an optionally substituted aryl or heteroaryl group and R1 represents an isopropyl group.
Dependencies are inferred from the claim text.