372-29-2

Usage

Uses

Used in Chemical Synthesis Industry:
Ethyl 3-amino-4,4,4-trifluorocrotonate is used as a building block for the synthesis of various chemical compounds. Its unique structure allows it to be a valuable intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. The presence of the amino and trifluoromethyl groups makes it a promising candidate for the development of new molecules with improved properties and applications.

InChI:InChI=1/C6H8F3NO2/c1-2-12-5(11)3-4(10)6(7,8)9/h10H,2-3H2,1H3/b10-4+

Upstream product

• 631-61-8 ammonium acetate 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 383-63-1 ethyl trifluoroacetate, 
• 141-78-6 ethyl acetate 

Downstream Products

• 453-32-7 3-Amino-4,4,4-trifluorbutyramid 
• 72850-81-8 Ethyl 2-phenoxy-4-(trifluoromethyl)-5-thiazolecarboxylate 
• 106203-24-1 4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester 
• 72850-80-7 Ethyl 2-fluoro-4-(trifluoromethyl)-5-thiazolecarboxylate 
• 72850-52-3 ethyl 2-chloro-4-(trifluoromethyl)thiazole-5-carboxylate 
• 151856-48-3 3-[4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione 
• 212755-12-9 3-(4-chloro-2,6-difluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione 
• 854122-75-1 2-chloro-5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-{[methyl(1-methylethyl)amino]sulfonyl}-benzamide 
• 119022-51-4 5-trifluoromethyl-3-hydroxy-1-methylpyrazole 
• 114136-76-4 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline 
• 37836-64-9 3-(4-chloro-phenyl)-6-trifluoromethyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF 6-(HALOALKYL)-2-HALO-5-ACYLPYRIDINES AND INTERMEDIATES FOR THIS PROCESS

The present invention relates to a process for preparing compounds of formula (I) (I), wherein R represents C1-C2-alkyl or C1-C2-haloalkyl, R1 represents C1-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, phenyl-C2-C4- alkenyl or phenyl-C2-C4-alkynyl, and X represents chlorine or bromine, by reacting a compound of formula (II) (II), wherein RA represents -CN or –COOH and R is defined as in formula (I), in a first step A) with a dehydroxyhalogenation agent selected from COCl2, diphosgene, triphosgene, cyanuric chloride, SOCl2, SO2Cl2, PCl3, PCl5, POCl3, PBr3, SOBr2 and SO2Br2, to arrive at a compound of formula (III) (III), wherein RB represents -CN or –COX, and X and R are defined as in formula (I), and the compound of formula (III) is reacted in step B) with a compound of formula (IV) R1M1(lV), - 41 - wherein M1 represents Li or MgY, wherein Y represents chlorine or bromine, and R1 is defined as in formula (I), and optionally further reacting the compound of formula (I) to a triazole derivative of formula (VIII) (VIII). It further relates to a process for preparing the compound of formula (II) and to particular compounds of formula (II) and (III).

Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl N2-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis

Alkyl N-aryl 1,2,3-triazole-carboxylates are important molecules or intermediates in medicinal chemistry, but the synthesis of N2-aryl counterparts remains elusive. Herein, we describe a Cu-mediated annulation reaction of alkyl 3-aminoacrylates with aryldiazonium salts, both of which are readily available substrates. Furthermore, alkyl 2-aminoacrylates are also viable substrates. Diverse alkyl N2-aryl 1,2,3-triazole-carboxylates and their analogues can be rapidly prepared under mild conditions. Especially, this protocol allows one to access several druglike variants of carbonic anhydrase inhibitors and celecoxib.

PREPARATION OF 6-HALO-2-(HALOALKYL)-3-ACYLPYRIDINES AND INTERMEDIATES THEREFOR

The present invention relates to a process for preparing compounds of formula (I) wherein R represents C1-C2-alkyl and X represents chlorine or bromine, by reacting a compound of formula (II) wherein R is defined as in formula (I), in a first step A) with a dehydroxyhalogenation agent selected from COCl2, diphosgene, triphosgene, cyanuric chloride, SOCI2, SO2CI2, PCI3, PCI5, POCI3, PBr3, SOBr2 and SO2Br2 to arrive at a compound of formula (III) wherein X and R are defined as in formula (I), and the compound of formula (III) is reacted in step B) with a malonate of formula (IV) wherein R1 represents C1-C6-alkyl, C2-C6, -alkenyl. C2-C6-alkynyl, C3-C8-cycloalkyl or benzyl; in presence of a base and a magnesium compound to arrive at a compound of formula (V) wherein X and R are defined as in formula (I); and R1 is defined as in formula (IV); and decarboxylating the compound of formula (V). Optionally the resulting compound of formula (I) is further reacted to a triazole derivative of formula (VIII). It further relates to the compounds of formula (V).

Identification of 5-(1-Methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)thiophene-2-Carboxamides as Novel and Selective Monoamine Oxidase B Inhibitors Used to Improve Memory and Cognition

Initial work in Drosophila and mice demonstrated that the transcription factor cyclic adenosine monophosphate (cAMP) response element binding protein (CREB) is a master control gene for memory formation. The relationship between CREB and memory has also been found to be true in other species, including aplysia and rats. It is thus well-established that CREB activation plays a central role in memory enhancement and that CREB is activated during memory formation. On the basis of these findings, a phenotypic high-throughput screening campaign utilizing a CRE-luciferase (CRE-Luci) SK-N-MC cell line was performed to identify compounds that enhance transcriptional activation of the CRE promoter with a suboptimal dose of forskolin. A number of small-molecule hits of unknown mechanisms of action were identified in the screening campaign, including HT-0411. Follow-up studies suggested that the CREB activation by HT-0411 is attributed to its specific and selective inhibition of monoamine oxidase B (MAO-B). Further, HT-0411 was shown to improve 24 h memory in rodents in a contextual fear conditioning model. This report describes the lead optimization of a series of 5-(1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl) thiophene-2-carboxamides that were identified as novel, potent, and selective inhibitors of MAO-B. Extensive SAR studies and in vivo behavioral evaluations of this and other related analogue series identified a number of potential clinical development candidates; ultimately, compound 8f was identified as a candidate molecule with high selectivity toward MAO-B (29-56 nM) over MAO-A (19% inhibition at a screening concentration of 50 μM), an excellent profile against a panel of other enzymes and receptors, good pharmacokinetic properties in rodents and dogs, and efficacy in multiple rodent memory models.

Method for preparing 3-amino-4,4,4-trifluorocrotonate

The invention discloses a method for preparing 3-amino-4,4,4-trifluorocrotonate with high raw material utilization rate. According to the invention, 4,4,4-trifluoroacetyl ethyl acetate and excessive ammonium acetate are subjected to an amination reaction to obtain a reaction solution, then the reaction solution is separated to an organic phase and an aqueous phase, ammoniacal liquor is added in the aqueous phase to obtain ammonium acetate, and finally ammonium acetate is cycled to continuous reaction.

Synthesis, Herbicidal Activity, and QSAR of Novel N-Benzothiazolyl- pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors

Protoporphyrinogen oxidase (PPO, E.C. 1.3.3.4) is known as a key action target for several structurally diverse herbicides. As a continuation of our research work on the development of new PPO-inhibiting herbicides, a series of novel 3-(2′-halo-5′-substituted-benzothiazol-1′-yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-diones 9 were designed and synthesized. The bioassay results indicated that a number of the newly synthesized compounds exhibited higher inhibition activity against tobacco PPO (mtPPO) than the controls, saflufenacil and sulfentrazone. Compound 9F-5 was identified as the most potent inhibitor with a Ki value of 0.0072 ΜM against mtPPO, showing about 4.2-fold and 1.4-fold higher potency than sulfentrazone (Ki = 0.03 ΜM) and saflufenacil (Ki = 0.01 ΜM), respectively. An additional green house assay demonstrated that compound 9F-6 (Ki = 0.012 ΜM) displayed the most promising postemergence herbicidal activity with a broad spectrum even at a concentration as low as 37.5 g of active ingredient (ai)/ha. Maize exhibits relative tolerance against compound 9F-6 at the dosage of 150 g ai/ha, but it is susceptible to saflufenacil even at 75 g ai/ha. Thus, compound 9F-6 exhibits the potential to be a new herbicide for weed control in maize fields.

Pyrimidine diketone compounds containing benzoxazine ring and application thereof

The invention discloses a kind of pyrimidine diketone compounds containing a benzoxazine ring and application thereof. The pyrimidine diketone compounds containing the benzoxazine ring are compounds with the structure shown as a general formula (1) in the specification, and in the formula (1), R1 is selected from hydrogen or an alkyl with the carbon atom number of 1-6, R2 is an ester with the carbon atom number of 2-10, and X is selected from halogen. The pyrimidine diketone compounds containing the benzoxazine ring possess high weeding activity.

Pyrimidinedione compound and application thereof

The present invention discloses a pyrimidinedione compound and an application thereof. The pyrimidinedione compound is a compound of the structure shown in the formula (1), wherein in the formula (1), R is selected from an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms or an ester group with 2 to 10 carbon atoms; X is selected from halogen; and Y is selected from O or S. The pyrimidindione compound disclosed by the present invention has high herbicidal activity .

Facile synthesis of pyrido[2,3-d]pyrimidines via cyclocondensation of 4,6-dichloro-2-methylsulfanylpyrimidine-5-carbaldehyde with β-substituted β-aminoacrylic esters

Abstract A new facile synthesis of pyrido[2,3-d]pyrimidin-4-ones via cyclocondensation of 4,6-dichloro-2-methylsulfanylpyrimidine-5-carbaldehyde with β-alkyl and β-aryl-β-aminoacrylic esters followed by hydrolysis of chlorine atom at position 4 of pyridopyrimidine ring has been developed. The cyclocondensation was found to be accelerated by acid.

METHOD FOR PRODUCING 3-AMINO-4,4,4-TRIFLUOROCROTONIC ACID ESTERS

The invention relates to a method for producing 3-amino-4,4,4-trifluorocrotonic acid esters of formula (I) or their E/Z isomers or tautomeric forms, whereby R1 and R2, independent of one another, represent hydrogen, an optionally substituted linear C1-C4 alkyl radical or an optionally substituted benzyl radical, and R3 represents methyl or ethyl. The inventive method is characterized in that: a) an alkyl trifluoroacetate is reacted with an alkyl acetate of formula CH3-CO-OR3 and with an alkali metal alcoholate to form an enolate of a trifluoroacetoacetic acid ester of formula (II), whereby M represents sodium or potassium, and R3 has the aforementioned meaning, and afterwards; b) the alkali enolate of the trifluoroacetoacetic acid ester from step a) can, without further purification, directly react with an amine of formula NHR1R2 in the presence of an acid to form 3-amino-4,4,4-trifluorocrotonic acid esters. This two-step method enables the production of 3-amino-4,4,4- trifluorocrotonic acid esters in high yields without resulting in the formation of significant byproducts.