2510-32-9

Usage

Uses

Used in Pharmaceutical Synthesis:
4-METHYL-1,3-OXAZOLE-5-CARBOXYLIC ACID is used as a key intermediate in the synthesis of highly selective α4β2-Nicotinic acetylcholine receptor agonists. These agonists are crucial in the treatment of cognitive disorders, as they help modulate the cholinergic system, which is often impaired in such conditions.
Used in Palladium-Catalyzed Cross-Coupling:
4-METHYL-1,3-OXAZOLE-5-CARBOXYLIC ACID is also utilized in the synthesis of small molecule human FPR1 receptor antagonists. These antagonists have potential applications in the treatment of various inflammatory diseases and other conditions related to the immune system.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-METHYL-1,3-OXAZOLE-5-CARBOXYLIC ACID is used as a reactant in a palladium-catalyzed cross-coupling reaction between heteroaryl carboxylic acids and aryl bromides. This reaction leads to the formation of arylated heterocycles, which are important structural motifs in various pharmaceuticals and agrochemicals.

InChI:InChI=1/C5H5NO3/c1-3-4(5(7)8)9-2-6-3/h2H,1H3,(H,7,8)

Upstream product

• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 77287-34-4 formamide 
• 18632-42-3 2-acetoxy-acetoacetic acid ethyl ester 
• 20485-39-6 ethyl 4-methyloxazole-5-carboxylate 

Downstream Products

• 953780-62-6 [4-(4-methyl-1,3-oxazol-5-yl)phenyl]acetic acid 
• 170959-40-7 5-(4-methyl-5-oxazoyl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione 
• 911297-49-9 6-[2-(4-methyl-oxazole-5-carbonyl)-phenyl]-hept-2-en-4-ynoic acid ethyl ester 
• 911297-36-4 (4-methyl-oxazol-5-yl)-[2-(1-methyl-3-trimethylsilanyl-prop-2-ynyl)-phenyl]methanone 
• 911297-48-8 (4-methyl-oxazol-5-yl)-[2-(1-methyl-prop-2-ynyl)-phenyl]methanone 
• 1008-29-3 4-methyl-5-phenyl-1,3-oxazole 
• 62348-24-7 4-Methyl-5-oxazolecarbonyl chloride 
• 693-93-6 4-methyloxazole 
• 3403-45-0 tert-butyl (4-methyloxazol-5-yl)carbamate 

Relevant academic research and scientific papers

Widely Exploited, Yet Unreported: Regiocontrolled Synthesis and the Suzuki–Miyaura Reactions of Bromooxazole Building Blocks

An approach to synthesis of 2-, 4-, and 5-bromooxazoles is described. The method was optimized, and its scope was extended to all three isomeric parents, as well as various alkyl- and aryl-substituted bromooxazoles. It was found that direct regiocontrolled lithiation followed by reaction with electrophilic bromine source was common for all substrates and led exclusively to the target substituted 2-, 4- and 5-bromooxazoles on multigram scale. The utility of the multipurpose building blocks obtained in this work was demonstrated in the Suzuki–Miyaura cross-coupling reaction under parallel synthesis conditions.

DOPAMINE D3 RECEPTOR ANTAGONISTS HAVING A MORPHOLINE MOIETY

The disclosure provides compounds of formula (I) or pharmaceutically acceptable salts thereof: The disclosure also provides processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them, and their use

DOPAMINE D3 RECEPTOR ANTAGONISTS HAVING A BICYCLO MOIETY

The disclosure provides compounds having formula (I), wherein the substituents are as defined herein. The compounds are useful for modulating the dopamine D3 receptor and for treating conditions associated therewith, such as addictions, drug dependency, and psychiatric conditions.

DOPAMINE D3 RECEPTOR ANTAGONISTS COMPOUNDS

The disclosure is directed to novel dopamine D3 receptor antagonists, processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, including treating drug dependency and psychosis.

Method for synthesizing furanosteroids

The present invention is a method for synthesizing furanosteroids. The method involves intramolecular Diels-Alder/retro-Diels-Alder reaction and tautomerization of a functionalized alkyne oxazole to produce a furo[2,3-b]phenol derivative which is elaborated by intermolecular and intramolecular condensations to generate ring-A of the furanosteroid. Furanosteroids and pharmaceutical compositions containing the same are also provided.

USE OF AZABICYCLO HEXANE DERIVATIVES

The present invention relates to the tartrate salt of 1-[2-fluoro-4-(trifluoromethyl)phenyl]-3-(3-{[4-methyl-5-(4-methyl-1,3-oxazol-5-yl)-4H-1,2,4-triazol-3-yl]thio}propyl)-3-azabicyclo[3.1.0]-hexane and solvates thereof, pharmaceutical formulations, proc

TRIAZOLYL DERIVATIVES OF AZABICYCLO [3.1.0] HEXANE AS DOPAMINE D3 RECEPTOR MODULATORS

The present invention relates to novel compounds of formula (IC) or a salt thereof, wherein p is an integer ranging from 0 to 4; R1 is independently selected from a group consisting of: halogen, hydroxy, cyano, C1-4alkyl,

TRIAZOLE DERIVATIVES AS MODULATORS OF DOPAMINE D3 RECEPTORS

The present invention relates to novel compounds of formula (I) or a salt thereof: wherein: G is a 5- or 6-membered heteroaromatic group, or is a 9- or 10-membered bicyclic heteroaromatic group containing one or two heteroatoms independently selected from nitrogen and oxygen, wherein G is not pyridyl, indazolyl or benzothiazolyl; p is an integer ranging from 0 to 4; R1 is independently selected from a group consisting of: halogen, hydroxy, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, C1-4alkanoyl or SF5; or corresponds to a group R5; R2 is hydrogen or C1-4alkyl; n is 2 or 3; X is S or -CH2-; R3 is C1-4alkyl; R4 is hydrogen, or a phenyl group, a heterocyclyl group, a 5- or 6-membered heteroaromatic group, or a 8- to 11-membered bicyclic group, any of which groups is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy and C1-4alkanoyl; R5 is isoxazolyl, -CH2-N-pyrrolyl, 1,1-dioxido-2-isothiazolidinyl, thienyl, thiazolyl, pyridyl or 2-pyrrolidinonyl, wherein each group is optionally substituted by one or two substituents selected from: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy and C1-4alkanoyl; processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, as modulators of dopamine D3 receptors, e.g. to treat substance related disorders, as antipsychotic agents, premature ejaculation or cognition impairment.

USE OF AZABICYCLO HEXANE DERIVATIVES

The present invention provides a new use of a compound of formula (I) or a pharmaceutically acceptable salt or solvate salt thereof, wherein: G is selected from a group consisting of: phenyl, pyridyl, benzothiazolyl, indazolyl; p is an integer ranging from 0 to 5; R1 is independently selected from a group consisting of: halogen, hydroxyl, cyano, C1-4alkyl, haloC1-4alkyl, C1-4 alkoxy, haloC1-4alkoxy, C1-4alkanoyl; or corresponds to a group R5; R2 is hydrogen or C1-4 alkyl; R3 I s C1-4alkyl; R4 is hydrogen, or a phenyl group, a heterocyclyl group, a 5- or 6-membered heteroaromatic group, or a 8- to 11-membered bicyclic group, any of which groups is optionally substituted by 1, 2, 3 or 4 substituents selected from the group consisting of: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, C1-4alkanoyl; R5 is a moiety selected from the group consisting of: isoxazolyl, -CH2-N-pyrrolyl, 1,1-dioxido-2-isothiazolidinyl, thienyl, thiazolyl, pyridyl, 2-pyrrolidinonyl, and such a group is optionally substituted by one or two substituents selected from: halogen, cyano, C1-4alkyl, haloC1-4alkyl, C1-4alkoxy, C1-4alkanoyl; and when R1 is chlorine and p is 1, such R1 is not present in the ortho position with respect to the linking bond to the rest of the molecule; and when R1 corresponds to R5, p is 1; in the manufacture of a medicament for the treatment of a somatoform disorder such as body dysmorphic disorder or hyperchondriasis, bulimia nervosa, anorexia nervosa, binge eating, paraphilia and nonparaphilic sexual addictions, Sydeham's chorea, torticollis, autism, a movement disorder including Tourette's syndrome; and in the manufacture of a medicament for the treatment of premature ejaculation.

Studies on the synthesis of furanosteroids. I. Viridin models

Alkyne oxazoles of general structure I are transformed directly to furo[2,3-b]phenol derivatives II by a sequence involving intramolecular Diels-Alder/retro-Diels-Alder reaction followed by tautomerization. Suitably functionalized phenols II undergo an intramolecular phenol-dienone-aldol condensation, generating the A,B,E-ring skeleton III characteristic of the viridin (1) class of furanosteroids.