1201080-09-2

Basic information

• Product Name: N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide
• Synonyms: N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide;Intermediate 1;Intermediate 1(KK-04-01)
• CAS NO: 1201080-09-2
• Molecular Formula: C₁₄H₁₃N₃O₃
• Molecular Weight: 271.27132
• Mol File: 1201080-09-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide(1201080-09-2)
• EPA Substance Registry System: N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide(1201080-09-2)

Safety Data

• Hazardous Substances Data: 1201080-09-2(Hazardous Substances Data)

Usage

Uses

As the provided materials do not specify any particular applications for N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide, it is not possible to list its uses based on the given information. However, given its structural features and potential pharmacological properties, it may find applications in various fields such as pharmaceuticals, agrochemicals, or materials science once its properties and potential uses are thoroughly investigated.

Upstream product

• 1201080-46-7 5-acetamido-4-ethoxy-2-nitrobenzoyl chloride 
• 1201080-20-7 methyl 3-acetamido-4-ethoxybenzoate 
• 1356916-92-1 3-acetamido-4-ethoxybenzoic acid 
• 1201080-29-6 5-acetamido-4-ethoxy-2-nitrobenzoic acid 
• 1201079-42-6 ethyl 3-(5-acetamido-4-ethoxy-2-nitrophenyl)-2-cyano-3-oxopropanoate 
• 1201079-16-4 N-[5-(2-cyanoacetyl)-2-ethoxy-4-nitrophenyl]acetamide 
• 1201079-19-7 N-{5-[2-cyano-3-(N,N-dimethylamino)acryloyl]-2-ethoxy-4-nitrophenyl}acetamide 
• 25351-89-7 N-(2-hydroxy-4-nitrophenyl)acetamide 
• 126360-59-6 methyl 3-(N-acetyl)amino-4-hydroxybenzoate 
• 116496-76-5 4-acetamido-3-ethoxynitrobenzene 
• 536-25-4 methyl 3-amino-4-hydroxybenzoate 
• 1571-72-8 3-amino-4-hydroxybenzoic acid 
• 121-88-0 5-Nitro-2-aminophenol 
• 848655-78-7 4-acetamido-3-ethoxyaniline 

Downstream Products

• 848133-76-6 7-ethoxy-6-acetylamino-4-chloro-quinoline-3-carbonitrile 
• 361162-95-0 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile 
• 915941-95-6 N-(4-[3-chloro-4-(pyridin-2-ylmethoxy)phenylamino]-3-cyano-7-ethoxyquinoline-6-yl)acetamide 
• 1233953-82-6 3-chloro-N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide 
• 848139-78-6 6-amino-4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-7-ethoxyquinoline-3-carbonitrile 
• 1360430-68-7 N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-morpholinopropanamide 
• 1233953-83-7 N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-piperidin-1-ylpropanamide 
• 1233953-81-5 N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-(dimethylamino)propanamide 
• 1360430-67-6 N-(4-((3-chloro-4-(pyridin-2-ylmethoxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)acrylamide 
• 1360430-66-5 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-morpholinopropanamide 
• 1360430-65-4 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-piperidin-1-ylpropanamide 
• 1360430-72-3 3-chloro-N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide 
• 1360430-64-3 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-(dimethylamino)propanamide 
• 1360430-63-2 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)acrylamide 

Relevant articles and documents

New synthesis of N-(4-chloro-3-cyano-7-ethoxyquinolin- 6-yl)acetamide

New synthetic route of N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)- acetamide (1) is described on a hectogram scale. The key steps include the intramolecular cyclization of 3-amino-2-(2-chlorobenzoyl)acrylonitrile 22 to give the 3-cyano-4-quinolone 7, which was chlorinated by POCl3 to give the final product 1 in 36.9% yield over 9 steps and 98.9% purity (HPLC). Purification methods of 7 and 1 were also given.

New and practical synthesis of N-(3-Cyano-7-ethoxy-4-oxo-1,4- dihydroquinolin-6-yl)acetamide

New and practical synthetic route of N-(3-cyano-7-ethoxy-4-oxo-1,4- dihydroquinolin-6-yl)acetamide (1) is described, through the cyclization of 2-aminophenyl-ethanone (12) with N,N-dimethylformamide dimethylacetal. The overall yield of 1 obtained from this process is 46% (five steps) with a purity of >99% (HPLC).

Irreversible inhibition of epidermal growth factor receptor activity by 3-aminopropanamides

Irreversible epidermal growth factor receptor (EGFR) inhibitors contain a reactive warhead which covalently interacts with a conserved cysteine residue in the kinase domain. The acrylamide fragment, a commonly employed warhead, effectively alkylates Cys797 of EGFR, but its reactivity can cause rapid metabolic deactivation or nonspecific reactions with off-targets. We describe here a new series of irreversible inhibitors containing a 3-aminopropanamide linked in position 6 to 4-anilinoquinazoline or 4-anilinoquinoline-3- carbonitrile driving portions. Some of these compounds proved to be as efficient as their acrylamide analogues in inhibiting EGFR-TK (TK = tyrosine kinase) autophosphorylation in A549 lung cancer cells. Moreover, several 3-aminopropanamides suppressed proliferation of gefitinib-resistant H1975 cells, harboring the T790M mutation in EGFR, at significantly lower concentrations than did gefitinib. A prototypical compound, N-(4-(3-bromoanilino)quinazolin-6- yl)-3-(dimethylamino)propanamide (5), did not show covalent binding to cell-free EGFR-TK in a fluorescence assay, while it underwent selective activation in the intracellular environment, releasing an acrylamide derivative which can react with thiol groups.

A new and improved process for N -(4-chloro-3-cyano-7-ethoxyquinolin-6-yl) acetamide

A new and improved synthetic route to N-(4-chloro-3-cyano-7-ethoxyquinolin- 6-yl)acetamide (1) is described on a kilogram scale. The key step is the basic cyclization of o-[(2-cyanovinyl)amino]benzoate (14) in tBuONa/ tBuOH system to give the 3-cyano-4-hydroxyquinoline (7). The final product 1 is obtained with 49% overall yield (seven steps) and 98.9% purity (HPLC), which makes it a cost-effective and commercially friendly process for scale-up operations.

Synthesis of n-(3-cyano-7-ethoxy-1,4-dihydro-4-oxoquinolin-6-yl)acetamide

New route for the preparation of N-(3-cyano-7-ethoxy-1,4-dihydro-4- oxoquinolin-6-yl)acetamide (1), a key intermediate for the synthesis of selective EGFR kinase inhibitors, was described.