68892-06-8

Usage

Uses

Used in Pharmaceutical Industry:
Methyl N-formyl-N-methylglycinate is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its ability to form carboxylic acids and amides makes it a valuable component in the creation of complex molecular structures.
Used in Agrochemical Industry:
In the agrochemical sector, methyl N-formyl-N-methylglycinate is employed as a precursor in the synthesis of agrochemicals, aiding in the production of effective and targeted pest control agents and other agricultural products.
Used in Fine Chemicals Production:
Methyl N-formyl-N-methylglycinate is utilized as a building block in the manufacture of fine chemicals, where its versatility allows for the creation of a wide range of specialty chemicals for various applications.
Used in Organic Synthesis:
As a reagent in organic synthesis, methyl N-formyl-N-methylglycinate is used for the formation of N-alkyl glycines and other complex organic compounds, showcasing its importance in the chemical industry for creating diverse chemical entities.

InChI:InChI=1/C5H9NO3/c1-6(4-7)3-5(8)9-2/h4H,3H2,1-2H3

Upstream product

• 107-31-3 Methyl formate 
• 13515-93-0 N-methylglycine methyl ester hydrochloride 
• 109-94-4 formic acid ethyl ester 
• 64-18-6 formic acid 

Downstream Products

• 487-59-2 α-N-methyltryptophan 
• 68892-07-9 1-methyl-5-carbomethoxy-2-thio-imidazole 
• 1421921-01-8 methyl N-{(E)-[(2,5-dimethyl-4-{[4-(4-methylphenyl)-1,3-thiazol-2-yl]methyl}phenyl)imino]methyl}-N-methylglycinate 

Relevant academic research and scientific papers

Targeting a Targeted Drug: An Approach Toward Hypoxia-Activatable Tyrosine Kinase Inhibitor Prodrugs

Tyrosine kinase inhibitors (TKIs), which have revolutionized cancer therapy over the past 15 years, are limited in their clinical application due to serious side effects. Therefore, we converted two approved TKIs (sunitinib and erlotinib) into 2-nitroimidazole-based hypoxia-activatable prodrugs. Kinetics studies showed very different stabilities over 24 h; however, fast reductive activation via E. coli nitroreductase could be confirmed for both panels. The anticancer activity and signaling inhibition of the compounds against various human cancer cell lines were evaluated in cell culture. These data, together with molecular docking simulations, revealed distinct differences in the impact of structural modifications on drug binding to the enzymes: whereas the catalytic pocket of the epidermal growth factor receptor (EGFR) accepted all new erlotinib derivatives, the vascular endothelial growth factor receptor (VEGFR)-inhibitory potential in the case of the sunitinib prodrugs was dramatically diminished by derivatization. In line, hypoxia dependency of ERK signaling inhibition was observed with the sunitinib prodrugs, while oxygen levels had no impact on the activity of the erlotinib derivatives. Overall, proof of principle could be shown for this concept, and the results obtained are an important basis for the future development of tyrosine kinase inhibitor prodrugs.

PHOSPHORAMIDATE ALKYLATOR PRODRUGS

Phosphoramidate alkylator prodrugs can be used to treat cancer when administered alone or in combination with one or more anti-neoplastic agents.

New mixed-ligand ReV complexes with bis(2-mercaptoethyl) sulfide and functionalized thioimidazolyl ligands

The preparation of the mixed-ligand ReV complexes [Re(O)(κ3-SSS)(κ1-Simz)] (1), [Re(O)(κ3-SSS)(κ1-Simz)]·HCl (2) and [Re(O)(κ3-SSS)(κ1-SimzCOGlyGly)] (3) are described. These [3+1] type compounds are stabilized by tridentate bis(2-mercaptoethyl) sulfide (HSSSH) and by monodentate functionalized thioimidazolyl ligands. Complexes 1, 2 and 3 were fully characterized by IR and 1H NMR spectroscopy, and by X-ray diffraction analysis in the case of 1 and 2. In complexes 1 and 2 the Re atom is five-coordinate, presenting a distorted square pyramidal coordination geometry. Based on the angular structural parameter, τ, this distortion lies towards a trigonal bipyramidal geometry (τ = 0.40, 1; τ = 0.46, 2). Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Convenient Synthesis of Methyl 1-Methyl-2,4-dibromo-5-imidazolecarboxylate

Three syntheses of methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8) are presented.One proceeds from sarcosine via ring closure, bromination, and desulfurization.The second uses N-methylimidazole, polybromination, and selective halogen-metal interchange.The third and most efficient and preparatively useful route begins with diaminomaleonitrile (13).Ring closure with triethyl orthoformate followed by methylation and hydrolysis affords 1-methyl-4,5-imidazoledicarboxylic acid (16).Regioselective decarboxylation followed by esterification yields methyl 1-methyl-5-imidazolecarboxylate (18).Subsequent dibromination gives the completely substituted imidazole 8.The primary purification in this sequence is fractional sublimation of 18 after the esterification step.An overall yield of 26percent is achieved from diaminomaleonitrile (13) to methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8), which is a key intermediate for the synthesis of tricyclic imidazo cooked food mutagens.