848133-76-6

Basic information

• Product Name: n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide
• Synonyms: N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl);n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide;N-(4-CHLORO-3-CYANO-7-ETHOXY-6-QUINOLINYL) ACETAMI;Acetamide, N-(4-chloro-3-cyano-7-ethoxy-6-quinolinyl)-;4-chloro-3-cyano-7-ethoxy-6-N-acetylquinoline;N-(4-chloro-3-cyano-7-ethoxyquinolin-6-yl)acetaMide;Neratinib Intermediate 2;n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide(848133-76-6)
• CAS NO: 848133-76-6
• Molecular Formula: C₁₄H₁₂ClN₃O₂
• Molecular Weight: 289.71698
• EINECS: 1592732-453-0
• Mol File: 848133-76-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 250°C(lit.)
• Boiling Point: 518.6 °C at 760 mmHg
• Flash Point: 267.5 °C
• Appearance: /
• Density: 1.35 g/cm³
• Vapor Pressure: 7.35E-11mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly, Heated)
• PKA: 13.13±0.43(Predicted)
• CAS DataBase Reference: n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide(848133-76-6)
• EPA Substance Registry System: n-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl) acetamide(848133-76-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 848133-76-6(Hazardous Substances Data)

Usage

Chemical Properties

yellow powder

Uses

N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide is used in synthesis of an antitumor agent, neratinib (N390090).

InChI:InChI=1/C14H12ClN3O2/c1-3-20-13-5-11-10(4-12(13)18-8(2)19)14(15)9(6-16)7-17-11/h4-5,7H,3H2,1-2H3,(H,18,19)

Upstream product

• 1222172-57-7 2-[(2-Cyanovinyl)amino]-4-ethoxy-5-acetylamido benzoylamide 
• 1222172-56-6 C₁₁H₁₅N₃O₃ 
• 28443-50-7 2-amino-5-chlorophenol 
• 860742-51-4 N-(4-chloro-2-ethoxyphenyl)acetamide 
• 16323-09-4 N-(4-chloro-2-hydroxyphenyl)acetamide 
• 108-24-7 acetic anhydride 
• 1356916-92-1 3-acetamido-4-ethoxybenzoic acid 
• 91004-38-5 3-acetamido-4-hydroxybenzoic acid 
• 1571-72-8 3-amino-4-hydroxybenzoic acid 
• 74896-30-3 1-<3-(acetylamino)-4-hydroxyphenyl>ethanone 
• 54255-50-4 3-amino-4-hydroxyacetophenone 
• 1201079-10-8 1-(5-acetamido-4-ethoxy-2-nitrophenyl)ethanone 
• 1201079-07-3 1-(3-acetamido-4-ethoxyphenyl)ethanone 
• 536-25-4 methyl 3-amino-4-hydroxybenzoate 

Downstream Products

• 848655-77-6 N-(4-(3-chloro-4-fluorophenylamino)-3-cyano-7-ethoxyquinolin-6-yl)acetamide 
• 1360430-63-2 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)acrylamide 
• 1360430-64-3 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-(dimethylamino)propanamide 
• 1360430-72-3 3-chloro-N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide 
• 1360430-65-4 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-piperidin-1-ylpropanamide 
• 1360430-66-5 N-(4-(3-chloro-4-fluoroanilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-morpholinopropanamide 
• 1360430-67-6 N-(4-((3-chloro-4-(pyridin-2-ylmethoxy)phenyl)amino)-3-cyano-7-ethoxyquinolin-6-yl)acrylamide 
• 1233953-81-5 N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-(dimethylamino)propanamide 
• 1233953-83-7 N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-piperidin-1-ylpropanamide 
• 1360430-68-7 N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)-3-morpholinopropanamide 
• 848139-78-6 6-amino-4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-7-ethoxyquinoline-3-carbonitrile 
• 1233953-82-6 3-chloro-N-(4-(3-chloro-4-(pyridin-2-ylmethoxy)anilino)-3-cyano-7-ethoxyquinolin-6-yl)propanamide 
• 361162-95-0 6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile 
• 848133-78-8 N-[4-(1-benzenesulfonyl-1H-indol-5-ylamino)-3-cyano-7-ethoxyquinolin-6-yl]acetamide 

Relevant articles and documents

Preparation method of disubstituted 4-chloroquinoline-3-carbonitrile derivative and preparation method of bosutinib

The invention provides a preparation method of a disubstituted 4-chloroquinoline-3-carbonitrile derivative and a preparation method of bosutinib. The preparation method of the disubstituted 4-chloroquinoline-3-carbonitrile derivative comprises the following steps: disubstituted o-nitrobenzoate (II) used as a raw material and acetonitrile are condensed under the action of an alkali to obtain a compound of formula III; the compound of formula III and a chloroformylating reagent undergo a chloroformylating reaction to obtain a compound of formula IV1 or formula IV2; and the compound of formula IV1 undergoes catalytic hydrogenation cyclization in the presence of a hydrogenation catalyst to prepare 7-[3-(4-methyl-1-piperazinyl)propoxy]-6-methoxy-4-chloroquinoline-3-carbonitrile (Ia), or the compound of formula IV2 is subjected to catalytic hydrogenation cyclization and anhydride amidation to prepare 6-acetamido-7-ethoxy-4-chloroquinolin-3-carbonitrile (Ib). The compound of formula Ia or Ibis used to prepare bosutinib, neratinib or pelitinib. The method of the invention has the advantages of short process flow, simplicity in operation, easiness in realization, low cost, few three wastes, high yield, high purity, and easiness in industrial production.

Clean production method of antitumor drug pelitinib intermediate

The invention belongs to the technical field of preparation of new drugs, and particularly relates to a clean production method of an antitumor drug pelitinib intermediate. According to the present invention, 3-cyano-4-hydroxy-6-acetamido-7-ethoxyquinoline is chlorinated by using phosphorus oxychloride as a chlorinating reagent and using an aromatic ring solvent under the catalysis of imidazoliumiodide to prepare the antitumor drug pelitinib intermediate 3-cyano-4-chloro-6-acetamido-7-ethoxyquinoline; and with the method, the consumption of phosphorus oxychloride is substantially reduced, wherein the good reaction conversion can be achieved only with 2.0 eq of phosphorus oxychloride so as to reduce the environmental protection pressure and improve the quality and the yield of the product.

Preparation method of Neratinib intermediate

The invention discloses a preparation method of a Neratinib intermediate. The preparation method comprises the following steps: by taking a compound A and POCl3 as raw materials, and a nitrogenous compound as a catalyst, allowing the compound A and POCl3 to react with the nitrogenous compound to obtain the Neratinib intermediate, wherein the compound A is (E)-N-(4-((2-cyano-3-morpholino-3-oxopropionic-1-alky-1-base)amino)-2-ethoxy phenyl) acetamide. According to the method, the nitrogenous compound is used as the catalyst, high temperature is not needed in the reaction, the reaction can be performed at the temperature of 65 to 75 DEG C, compared with the traditional method requiring the high temperature of 200 to 250 DEG C, the reaction temperature is greatly reduced, the high-temperature reaction is avoided, operation safety is ensured, the reaction yield is also increased to 45 to 57 percent, and the yield is obviously increased.