1222172-51-1

Basic information

• Product Name: Ethyl 5-acetamido-2-amino-4-ethoxybenzoate
• Synonyms: Benzoic acid, 5-(acetylamino)-2-amino-4-ethoxy-, ethyl ester
• CAS NO: 1222172-51-1
• Molecular Formula: C13H18N2O4
• Molecular Weight: 266.297
• Mol File: 1222172-51-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Ethyl 5-acetamido-2-amino-4-ethoxybenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 5-acetamido-2-amino-4-ethoxybenzoate(1222172-51-1)
• EPA Substance Registry System: Ethyl 5-acetamido-2-amino-4-ethoxybenzoate(1222172-51-1)

Safety Data

• Hazardous Substances Data: 1222172-51-1(Hazardous Substances Data)

Upstream product

• 19013-10-6 ethyl 4-hydroxy-3-nitrobenzoate 
• 198704-99-3 ethyl 3-acetamido-4-hydroxybenzoate 
• 1356916-92-1 3-acetamido-4-ethoxybenzoic acid 
• 91004-38-5 3-acetamido-4-hydroxybenzoic acid 
• 1571-72-8 3-amino-4-hydroxybenzoic acid 
• 780821-04-7 ethyl 3-acetamido-4-ethoxybenzoate 

Downstream Products

• 1222172-52-2 ethyl 2-[(2-cyanovinyl)amino]-4-ethoxy-5-acetylamidobenzoate 
• 848133-76-6 7-ethoxy-6-acetylamino-4-chloro-quinoline-3-carbonitrile 
• 848133-75-5 3-cyano-4-hydroxyl-6-acetamido-7-ethoxyquinoline 
• 1269662-90-9 N⁴-(3-chloro-4-fluorophenyl)-7-ethoxyquinazoline-4,6-diamine 

Relevant articles and documents

Balancing reactivity and antitumor activity: heteroarylthioacetamide derivatives as potent and time-dependent inhibitors of EGFR

Second- and third-generation inhibitors of EGFR possess an acrylamide group which alkylates Cys797, allowing to overcome resistance due to insurgence of T790M mutation. Less reactive warheads, yet capable to bind the target cysteine, may be useful to design newer and safer inhibitors. In the present work, we synthesized a 2-chloro-N-(4-(phenylamino)quinazolin-6-yl)acetamide (8) derivative as a prototype of EGFR inhibitor potentially able to react with Cys797 by nucleophilic substitution. We then tuned the reactivity of the acetamide fragment by replacing the chlorine leaving group with (hetero)-aromatic thiols or carboxylate esters. Among the synthesized derivatives, the 2-((1H-imidazol-2-yl)thio)acetamide 16, while showing negligible reactivity with cysteine in solution, caused long-lasting inhibition of wild-type EGFR autophosphorylation in A549 cells, resulted able to bind recombinant EGFR L858R/T790M in a time-dependent manner, and inhibited both EGFR autophosphorylation and proliferation in gefitinib-resistant H1975 lung cancer cells (expressing EGFR L858R/T790M mutant) at low micromolar concentration.

PREPARATION METHODS OF 6-SUBSTITUTED AMINO-3-CYANOQUINOLINE COMPOUNDS AND THE INTERMEDIATES THEREOF

The present invention relates to a method for preparing 6-substituted amino-3-cyanoquinoline compounds (compound A for short) and the intermediates thereof, more particularly, to a compound of the following formula (I), the preparation method thereof, the intermediates thereof and use thereof for preparing the compound A. The compound of the formula (I) is cyclized in the presence of an alkali to give a compound of formula A, wherein W is OH; or the compound of the formula (I) is cyclized in the presence of an alkali, and then chlorinated to give a compound of the formula A, wherein W is Cl. Compared with the known methods in the literature, the method for preparing the compound A from the compound of formula (I) according to the present invention can avoid using high-temperature condition and high boiling point solvents, and is safe and environment-friendly, mild in reaction condition, easy in operation with a high yield and high product purity.