390386-23-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Thiazolecarboxamide,2-(1-methylethyl)-(9CI) is used as an intermediate in the synthesis of pharmaceuticals for its antifungal and anticancer properties. It contributes to the development of drugs that target fungal infections and cancer cells, offering potential therapeutic benefits in treating these conditions.
Used in Agrochemical Industry:
4-Thiazolecarboxamide,2-(1-methylethyl)-(9CI) is also used as an intermediate in the synthesis of agrochemicals, particularly in the development of fungicides and pesticides. Its antifungal properties make it a valuable component in creating effective solutions to protect crops from fungal diseases, thereby enhancing agricultural productivity and crop yield.

Upstream product

• 133047-44-6 2-isopropyl-thiazole-4-carboxylic acid ethyl ester 
• 6620-69-5 2-isopropyl-4,5-dihydro-thiazole-4-carboxylic acid ethyl ester 
• 336193-96-5 methyl 2-isopropylthiazole-4-carboxylate 
• 416858-66-7 2-isopropenyl-thiazole-4-carboxylic acid methyl ester 
• 76275-87-1 methyl 2-acetylthiazole-4-carboxylate 

Downstream Products

• 848555-18-0 2-isopropylthiazole-4-carbonitrile 
• 917878-56-9 5-(2'-isopropyl[2,4']bithiazolyl-4-ylmethylnesulfonyl)-1-phenyl-1H-tetrazole 
• 917878-64-9 5-(2'-isopropyl[2,4']bithiazolyl-4-ylmethylsulfanyl)-1-phenyl-1H-tetrazole 
• 390386-36-4 (R)-4-benzyl-3-[(2R,3S)-(E)-3-hydroxy-5-(2'-isopropyl[2,4']bithiazolyl-4-yl)-2-methylpent-4-enoyl]oxazolidin-2-one 

Relevant academic research and scientific papers

New total synthesis of (+)-cystothiazole A based on palladium-catalyzed cyclization-methoxycarbonylation

Palladium-catalyzed cyclization-methoxycarbonylation of (2R,3S)-3-methylpenta-4-yne-1,2-diol (6) derived from (2R,3S)-epoxy butanoate 7 followed by methylation gave the tetrahydro-2-furylidene acetate (-)-10, which was converted to the left-half aldehyde

New total synthesis of (+)-cystothiazole A

Palladium-catalyzed cyclization-methoxycarbonylation of (2R,3S)-3-methylpenta-4-yne-1,2-diol (7) derived from (2R,3S)-epoxy butanoate 8 followed by methylation gave the tetrahydro-2-furylidene acetate (-)-9, which was converted to the left-half aldehyde (

Alternative synthesis of cystothiazole A

Palladium-catalyzed methoxycarbonylation of (-)-(2R,3S)-1-tert-butyldimethylsiloxy-3-methyl-2-methoxypenta-4-yne 9 derived from (2R,3S)-epoxy butanoate 5 gave the acetylenic ester 10, which was treated with MeOH in the presence of Bu3P to affor

SUBSTITUTED PIPERAZINES OF AZEPINES, OXAZEPINES, AND THIAZEPINES

Described herein are antipyschotic compounds of formula (I) wherein: is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, O, and S; R1 is hydrogen, (C1-6) fluoroalkyl, (C3-6) cycloalkyl, or (C1-4) alkyl, wherein the (C1-4) alkyl is unsubstituted or substituted with hydroxy, methoxy, ethoxy, OCH2CH2OH, -CN, imidazolidin-2-one, phenyl, or tetrazole wherein tetrazole is unsubstituted or substituted with (C1-4) alkyl; R2 is H, halogen, (C1-6) fluoroalkyl, (C3-6) cycloalkyl, OR6, SR6, NO2, CN, COR6, C(O)OR6, C(OH)R6, CONR7R8, phenyl or (C1-6) alkyl, wherein the (C1-6) alkyl is unsubstituted or substituted with a hydroxy; R3 is hydrogen, (C 1-6)fluoroalkyl , (C3-6) cycloalkyl, (C2-6) alkenyl, phenyl, monocyclic heteroaromatic, bicyclic heteroaromatic, or (C1-4)alkyl wherein (C1-4) alkyl is unsubstituted or substituted with a phenyl; R4 and R5 are independently selected from hydrogen, halogen, (C1-6) alkyl, (C1-6) fluoroalkyl, OR9, SR9, NO2, CN, or COR9; R6 is hydrogen, (C1-6) fluoroalkyl, or (C1-6) alkyl; R7 and R8 are independently hydrogen, or (C1-6) alkyl; R9 is hydrogen, (C1-6) fluoroalkyl, (C1-6) alkyl; Alk is (C1-4) alkylene unsubstituted or substituted with a hydroxy; Y is oxygen, sulfur, SO2, or a bond; X is CH2, C=O, S, O, or SO2; Z is hydrogen, halogen, (C1-6) alkyl, (C1-6)fluoroalkyl, -OH, (C1-6) alkoxy, (C1-6) fluoroalkoxy, (C1-6) alkylthio, (C1-6) acyl, (C1-4)alkylsulfonyl, -OCF3, -NO2, - CN, carboxamido which may be substituted on the nitrogen by one or two (C1-4) alkyl groups, and -NH2 in which one of the hydrogens may be replaced by a (C1-4) alkyl group and the other hydrogen may be replaced by either a (C1-4) alkyl group, a (C1-6) acyl group, or a (C1-4) alkylsulfonyl group; the phenyl of R1, R2 or R3 is independently unsubstituted or substituted with one to three substituents independently selected from Z; the monocyclic heteroaromatic of R3 is unsubstituted or substituted with one to three substituents independently selected from Z; the bicyclic heteroaromatic of R3 is unsubstituted or substituted with one to three substituents independently selected from Z; and salts, solvates, and crystal forms thereof. Also described are the use of the compounds of formula (I) as antagonists of the dopamine D2 receptor and as agents for the treatment of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I).

Total synthesis of cystothiazoles A and C

An efficient pathway culminating in the enantiocontrolled preparation of cystothiazoles A and C has been described. The cystothiazoles demonstrate potent antifungal activity and function as novel inhibitors of mitochondrial oxidation at a specific site on the cytochrome bc1 complex. These studies outline a general and flexible plan that can be readily adapted for the synthesis of a variety of related five-membered heterocyclic systems and for biological investigations of structure-activity relationships. The core [2,4′]bisthiazole component 8 was prepared in six steps, and the use of the Horner-Emmons olefination to yield the α,β-unsaturated ester 10 set the stage for an asymmetric Evans aldol process, which established the required C4/C5 stereochemistry. Finally the cystothiazoles A and C were prepared via a stereocontrolled O-alkylation of the precursor β-keto esters 22a and 22b.