208465-72-9

Usage

Uses

Used in Pharmaceutical Industry:
METHYL (2-CHLOROMETHYL)OXAZOLE-4-CARBOXYLATE is used as an intermediate for the synthesis of various pharmaceuticals. Its unique structure and reactivity contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL (2-CHLOROMETHYL)OXAZOLE-4-CARBOXYLATE is utilized as a precursor in the production of agrochemicals. Its properties allow for the creation of compounds that can be used in pest control and crop protection, enhancing agricultural productivity.
Used in Organic Synthesis:
METHYL (2-CHLOROMETHYL)OXAZOLE-4-CARBOXYLATE is employed as a versatile building block in organic synthesis. Its stability and reactivity make it suitable for the construction of complex organic molecules, which can be applied in various fields such as materials science, chemical research, and the development of new compounds with specific properties.
Used as a Reagent in Chemical Transformations:
Due to its chloromethyl group, METHYL (2-CHLOROMETHYL)OXAZOLE-4-CARBOXYLATE is used as a reagent in a variety of chemical transformations and reactions. It facilitates the synthesis of new compounds and the modification of existing ones, broadening the scope of chemical research and development.

InChI:InChI=1/C6H6ClNO3/c1-10-6(9)4-3-11-5(2-7)8-4/h3H,2H2,1H3

Upstream product

• 289030-37-1 2-dichloromethyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester 
• 124-41-4 sodium methylate 
• 3018-12-0 dichloroacetonitrile 
• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 
• 866324-08-5 methyl 2-(dichloromethyl)-1,3-oxazole-4-carboxylate 
• 175551-77-6 methyl 2-(bromomethyl)oxazole-4-carboxylate 

Downstream Products

• 391208-72-3 (4R),(6R)-6-(2-chloromethyloxazol-4-yl)-6-hydroxy-4-tert-butyldiphenylsilanyloxyhex-1-ene 
• 391208-71-2 (4R),(6R)-6-(2-chloromethyloxazol-4-yl)-6-tert-butyldimethylsilanyloxy-4-tert-butyldiphenylsilanyloxyhex-1-ene 
• 391208-74-5 (1R,3R)-3-(tert-butyldiphenylsilanyloxy)-1-(2-((E)-3-((2R,3S,4S,5S,6R)-3,5-dimethyl-6-((E)-2-(2-methyloxazol-4-yl)prop-1-en-2-yl)-4-(triisopropylsilanyloxy)tetrahydro-2H-pyran-2-yl)prop-1-enyl)oxazol-4-yl)hex-5-en-1-ol 
• 1097777-99-5 methyl 2-{[5-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)-1H-indol-1-yl]methyl}-1,3-oxazole-4-carboxylate 
• 1097777-98-4 2-{[5-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)-1H-indol-1-yl]methyl}-1,3-oxazole-4-carboxylic acid 
• 1263298-97-0 Methyl 2-(5-methoxy-2-phenylindol-1-ylmethyl)oxazole-4-carboxylate 
• 866324-13-2 2-[(4R,6R,7E)-4,6-bis(tert-butyldimethylsilyloxy)-2-oxo-8-phenyl-7-octenyl]oxazole-4-carboxylic acid methyl ester 

Relevant academic research and scientific papers

An efficient, practical approach to the synthesis of 2,4-disubstituted thiazoles and oxazoles: Application to the synthesis of GW475151

GlaxoWellcome Research and Development, Chemical Development Division, Medicines Research Centre,. A new method for the synthesis of 2,4-disubstituted oxazoles and thiazoles and 2,4,5-trisubstituted oxazoles from readily available starting materials is described. The methodology has been applied on multigram scale and involves transfer of oxidation state through a molecular framework. In particular the oxazole-containing amino acid fragment of the 5,5-transfused lactam GW475151, 1, has been prepared in excellent yield and purity.

A new method for the formation of 2,4-disubstituted oxazoles: Internal transfer of oxidation state through a molecular framework

A new method for the synthesis of 2,4-disubstituted oxazoles is described from readily available starting materials. The synthesis avoids the necessity for the oxidation of an oxazoline to an oxazole by utilising an internal transfer of oxidation state across a molecular framework and has been performed on multigram scale. (C) 2000 Elsevier Science Ltd.

Facile synthesis of autophagonizer and evaluation of its activity to induce autophagic cell death in apoptosis-defective cell line

Some cancer cells are resistant to apoptosis, rendering them irresponsive towards apoptosis-inducing chemotherapy drugs. Another mode of action to kill these apoptosis-defective cells is essential and autophagy, a dynamic process that degrades cytoplasmic contents for cellular maintenance, has been considered as one of the alternate routes. A small molecule inducer of autophagy, autophagonizer was reported to induce cell death through a novel process that is independent of extrinsic apoptosis and the normal signaling pathways of autophagy. Here, we describe an efficient synthetic procedure for the autophagonizer. The newly synthesized autophagonizer (DK-1-49) resulted in an accumulation of autophagy-associated LC3-II and enhanced levels of autophagosomes and acidic vacuoles. Furthermore, cell viability was inhibited by autophagic cell death in not only human cancer cells but also Bax/Bak double-knockout cells. These findings highlight that intrinsic apoptosis is not also involved in the induction of cellular death by the autophagonizer suggesting the autophagonizer is a promising candidate for anticancer therapeutics for cancer cells that are resistant to apoptosis-inducing chemotherapy.

MACROCYCLIC FUSED PYRRAZOLES AS MCL-1 INHIBITORS

Provided are compounds represented by Formula IA: (IA), and the pharmaceutically acceptable salts and solvates thereof, wherein R, R 1a, R 1b, L 1, L 2, L 3, X, A, B and C are as defined as set forth

HETEROCYCLIC MITOCHONDRIAL ACTIVITY INHIBITORS AND USES THEREOF

Heterocyclic compounds of Formula (I) and pharmaceutically acceptable salt thereof are disclosed. The use of such heterocyclic compounds and pharmaceutically acceptable salt thereof for the treatment of cancers, and more particularly cancers sensitive to mitochondrial activity inhibition and increased reactive oxygen species (ROS) levels, is also disclosed. Such cancers include acute myeloid leukemia (AML), preferably AML characterized by certain features, such as high level of expression of one or more Homeobox (HOX)-network genes, high and/or low expression of specific genes, the presence of one or more cytogenetic or molecular risk factors such as intermediate cytogenetic risk, Normal Karyotype (A/K), mutated NPM1, mutated CEBPA, mutated FLT3, mutated DNMT3A, mutated TET2, mutated IDH1, mutated IDH2, mutated RUNX1, mutated WT1, mutated SRSF2, intermediate cytogenetic risk with abnormal karyotype (intern(abnK)), trisomy 8 (+8) and/or abnormal chromosome (5/7), and/or a high leukemic stem cell (LSC) frequency.

N-[2-(3-AMINO-2,5-DIMETHYL-1,1-DIOXIDO-5,6-DIHYDRO-2H-1,2,4-THIADIAZIN-5-YL)-1,3-THIAZOL-4-YL] AMIDES USEFUL AS BACE INHIBITORS

The present invention is directed to compounds, tautomers and pharmaceutically acceptable salts of the compounds which are disclosed, wherein the compounds have the structure of Formula I, wherein the variables R1, R2 and R3/su

N-[2-(2-AMINO-6,6-DISUBSTITUTED-4, 4A, 5, 6-TETRAHYDROPYRANO [3,4-D][1,3] THIAZIN-8A (8H)-YL) -1, 3-THIAZOL-4-YL] AMIDES

The present invention is directed to compounds, tautomers and pharmaceutically acceptable salts of the compounds which are disclosed, wherein the compounds have the structure of Formula (I), and the variables R1, R2 and R3

Development of a practical and scalable route for the preparation of the deacetoxytubuvaline (dTuv) fragment of pretubulysin and analogs

We present herein a novel and convenient route for the scaling-up of the dTuv fragment of pretubulysin. The newly conceived chemical path involves a practical and efficient one-step procedure for the preparation of a key thiazole intermediate, followed by high-yielding Wittig olefination/reduction steps. The optimized route, starting from the inexpensive and non-toxic l-cysteine, encompasses five synthetic steps and only two chromatographic purifications, thus displaying a dramatically increased overall yield. The versatility of the proposed approach also provides new hints for the exploration of pretubulysin derivatives bearing diverse heterocyclic portions.

2-AMINO-6-METHYL-4,4a,5,6-TETRAHYDROPYRANO[3,4-d][1,3]THIAZIN-8a(8H)-YL-1,3-THIAZOL-4-YL AMIDES

The present invention is directed to compounds, tautomers and pharmaceutically acceptable salts of the compounds which are disclosed, wherein the compounds have the structure of Formula (I), and the variable R1 is as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

Incorporation of heterocycles into the backbone of peptoids to generate diverse peptoid-inspired one bead one compound libraries

Combinatorial libraries of peptoids (oligo-N-substituted glycines) have proven to be useful sources of protein ligands. Each unit of the peptoid oligomer is derived from 2-haloacetic acid and a primary amine. To increase the chemical diversity available in peptoid libraries, we demonstrate here that heterocyclic halomethyl carboxylic acids can be employed as backbone building blocks in the synthesis of peptoid-based oligomers. Optimized conditions are reported that allow the creation of large, high quality combinatorial libraries containing these units.