52009-53-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Chloro-3,4-dimethoxybenzoic acid is used as a starting material for the synthesis of various pharmaceutical compounds. Its unique structure allows for further chemical modifications and functionalization, making it a valuable intermediate in the development of new drugs.
Used in the Synthesis of 14C-labelled N-(2-chloro-3,4-dimethoxybenzylideneamino)guanidinium acetate:
In the field of radiochemistry, 2-chloro-3,4-dimethoxybenzoic acid serves as a key starting material in the four-step synthesis of 14C-labelled N-(2-chloro-3,4-dimethoxybenzylideneamino)guanidinium acetate. This radiolabeled compound has potential applications in medical imaging and diagnostic procedures, particularly in the detection and monitoring of various diseases and conditions.

InChI:InChI=1/C9H9ClO4/c1-13-6-4-3-5(9(11)12)7(10)8(6)14-2/h3-4H,1-2H3,(H,11,12)

Upstream product

• 93-07-2 Veratric acid 
• 925-90-6 ethylmagnesium bromide 
• 5417-17-4 2-chloro-3,4-dimethoxybenzaldehyde 

Downstream Products

• 352437-41-3 (2-chloro-3,4-dimethoxyphenyl)-N-[(4,5-dimethylimidazol-2-yl)methyl]-N-(3-methylbutyl)carboxamide 
• 209204-23-9 2-chloro-3,4-dimethoxybenzoyl chloride 
• 1349175-51-4 2-chloro-N-(3,5-dichloropyridin-4-yl)-3,4-dimethoxybenzamide 
• 5417-17-4 2-chloro-3,4-dimethoxybenzaldehyde 
• 1407155-96-7 2-chloro-3,4-bis((4-methoxybenzyl)oxy)-N-(pyridin-4-yl)benzamide 
• 1338705-94-4 2-chloro-3,4-bis((4-methoxybenzyl)oxy)-N-(((1S,4S)-2-methyl-2-azabicyclo[2.2.1]heptan-5-yl)methyl)benzamide 
• 1338706-20-9 (2-chloro-3,4-bis((4-methoxybenzyl)oxy)phenyl) ((3aR,6aS)-5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone 
• 1338707-57-5 2-chloro-3,4-bis((4-methoxybenzyl)oxy)-N-((1u202fR,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl)benzamide 
• 1338706-11-8 (S)-(2-chloro-3,4-bis((4-methoxybenzyl)oxy)phenyl) (hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)methanone 
• 1338705-87-5 (1,4-diazabicyclo[3.2.2]nonan-4-yl) (2-chloro-3,4-bis((4-methoxybenzyl)oxy)phenyl)methanone 
• 1338706-33-4 (2-chloro-3,4-bis((4-methoxybenzyl)oxy)phenyl) (4-(dimethylamino)piperidin-1-yl)methanone 
• 1338706-30-1 (R)-(2-chloro-3,4-bis((4-methoxybenzyl)oxy)phenyl) (3-(dimethylamino)pyrrolidin-1-yl)methanone 
• 1407155-91-2 2-chloro-N-(2-(dimethylamino)ethyl)-3,4-bis((4-methoxybenzyl)oxy)benzamide 
• 137054-47-8 (2-chloro-3,4-bis((4-methoxybenzyl)oxy)phenyl)(4-methylpiperazin-1-yl)methanone 

Relevant academic research and scientific papers

SUBSTITUTED BENZAMIDES AS MODULATORS OF TREX1

Provided are compounds of Formula (I): (I) and pharmaceutically acceptable salts and compositions thereof, which are useful for treating a variety of conditions associated with TREX1.

Cefiderocol (S-649266), A new siderophore cephalosporin exhibiting potent activities against Pseudomonas aeruginosa and other gram-negative pathogens including multi-drug resistant bacteria: Structure activity relationship

The structure-activity relationship (SAR) for a novel series of catechol conjugated siderophore cephalosporins is described with their in vitro activities against multi-drug resistant Gram-negative pathogens including Pseudomonas aeruginosa, Acinetobacter baumannii, Stenotrophomonas maltophilia and Enterobacteriaceae. Cefiderocol (3) was one of the best molecules which displayed well-balanced and potent activities against multi-drug resistant Gram-negative pathogens including carbapenem resistant bacteria among the prepared compounds with the modified C-7 side chain and the modified C-3 side chain. Cefiderocol (3) is a highly promising parenteral cephalosporin for the treatment of multi-drug resistant Gram-negative infection.

Competition of substituents for ortho direction of metalation of veratric acid

LTMP (5 equiv) metalates randomly veratric acid (1). Under external quench conditions, the thermodynamically more stable lithium 2-lithio-3,4-dimethoxybenzoate (2) reacts with a variety of electrophiles to give versatile building units that are not easily accessible by conventional means. Under in situ quench conditions (LTMP/TMSCl), a reversal of regioselectivity is observed and 6-trimethylsilyl-3,4-dimethoxybenzoic acid (10) is formed predominantly.

Synthesis of N-(2-chloro-3,4-dimethoxybenzylideneamino)guanidinium acetate [α-14C]

14C-Labelled N-(2-chloro-3,4-dimethoxybenzylideneamino)guanidinium acetate has been synthesized as a part of a four-step procedure which involved decarboxylation of 2-chloro-3,4-dimethoxybenzoic acid by Pb(OAc)4 to give 2-chloro-3,4-dimethoxy-1-iodobenzene, followed by a selective lithiation at the iodine position and electrophilic substitution with N,N-dimethylformamide [α-14C] and final reaction with aminoguanidine bicarbonate. The specific activity was 59 mCi/mmol and the overall yield 49%. Copyright