923289-36-5

Basic information

• Product Name: Ethanone, 1-(2-amino-3-chloro-4-methoxyphenyl)-
• Synonyms: Ethanone, 1-(2-amino-3-chloro-4-methoxyphenyl)-;6-ACETYL-2-CHLORO-3-METHOXY ANILINE;1-(2-Amino-3-chloro-4-methoxyphenyl)ethanone;(2-Amino-3-chloro-4-methoxyphenyl)acetone;1-(2-Amino-3-chloro-4-methoxyphenyl)ethan-1-one, 6-Acetyl-2-chloro-3-methoxyaniline, 4-Acetyl-3-amino-2-chloroanisole;2'-Amino-3'-chloro-4'-methoxyacetophenone;1-(2-aMino-3-chloro-4-Methoxyphenyl)ethan-1-one;1-(2-Amino-3-chloro-4-methoxyphenyl)
• CAS NO: 923289-36-5
• Molecular Formula: C₉H₁₀ClNO₂
• Molecular Weight: 199.63
• Product Categories: Drug Intermediates;API intermediates
• Mol File: 923289-36-5.mol

Chemical Properties

• Boiling Point: 366.8ºC at 760 mmHg
• Flash Point: 175.6ºC
• Appearance: /
• Density: 1.259 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: Ethanone, 1-(2-amino-3-chloro-4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(2-amino-3-chloro-4-methoxyphenyl)-(923289-36-5)
• EPA Substance Registry System: Ethanone, 1-(2-amino-3-chloro-4-methoxyphenyl)-(923289-36-5)

Safety Data

• Hazardous Substances Data: 923289-36-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Ethanone, 1-(2-amino-3-chloro-4-methoxyphenyl)is used as a synthetic intermediate for the development of new drugs and treatments. Its unique chemical structure and properties contribute to the discovery of bioactive molecules with potential therapeutic applications.
Used in Cancer Treatment Research:
In the field of oncology, Ethanone, 1-(2-amino-3-chloro-4-methoxyphenyl)is used as a research compound to explore its potential in cancer treatment. Its chemical properties may offer insights into the development of novel therapeutic agents that target specific cancer-related pathways or mechanisms.
Used in Synthesis of Bioactive Molecules:
Ethanone, 1-(2-amino-3-chloro-4-methoxyphenyl)is utilized in the synthesis of various bioactive molecules, which can be further studied and optimized for their therapeutic potential. Its role in the synthesis process highlights its importance in the development of innovative pharmaceutical compounds.

InChI:InChI=1/C9H10ClNO2/c1-5(12)6-3-4-7(13-2)8(10)9(6)11/h3-4H,11H2,1-2H3

Upstream product

• 75-05-8 acetonitrile 
• 113206-03-4 2-chloro-3-methoxyphenylamine 

Downstream Products

• 1098189-05-9 2-isopropylamino-thiazole-4-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)phenyl]amide 
• 1098189-15-1 vedroprevir 
• 1310551-61-1 6-Isopropyl-pyridine-2-carboxylic acid [6-acetyl-2-chloro-3-(2-methoxy-ethoxy)-phenyl]-amide 
• 1098201-26-3 1-[2-amino-3-chloro-4-(2-methoxy-ethoxy)-phenyl]-ethanone 
• 1310551-56-4 4-Isopropyl-thiazole-2-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide 
• 1310551-52-0 2-Isopropyl-thiazole-4-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide 
• 1098189-01-5 1-[2-amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone 
• 1098189-00-4 1-(2-amino-3-chloro-4-hydroxy-phenyl)-ethanone 
• 1180495-68-4 N-(6-acetyl-2-chloro-3-methoxyphenyl)-2-isopropylthiazole-4-carboxamide 
• 1180495-62-8 N-(6-acetyl-2-chloro-3-methoxyphenyl)-5-isopropylisoxazole-3-carboxamide 
• 1180496-15-4 N-(6-acetyl-2-chloro-3-methoxyphenyl)-2-(trifluoromethyl)thiazole-4-carboxamide 
• 1180496-00-7 N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-bromothiazole-2-carboxamide 
• 1180496-29-0 N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-cyclopropylthiazole-2-carboxamide 
• 1180495-36-6 N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-trifluoromethylthiazole-2-carboxamide 

Relevant articles and documents

Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350

SAR analysis performed with a limited set of cyclopentane-containing macrocycles led to the identification of N-[17-[2-(4-isopropylthiazole-2-yl)-7-methoxy-8-methylquinolin-4-yloxy]- 13-methyl-2,14-dioxo-3,13-diazatricyclo [13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamid e (TMC435350, 32c) as a potent inhibitor of HCV NS3/4A protease (Ki = 0.36 nM) and viral replication (replicon EC50 = 7.8 nM). TMC435350 also displayed low in vitro clearance and high permeability, which were confirmed by in vivo pharmacokinetic studies. TMC435350 is currently being evaluated in the clinics.

Discovery of novel potent and selective dipeptide hepatitis C virus NS3/4A serine protease inhibitors

Starting from the previously reported HCV NS3/4A protease inhibitor BILN 2061 (1), we have used a fast-follower approach to identify a novel series of HCV NS3/4A protease inhibitors in which (i) the P3 amino moiety and its capping group have been truncated, (ii) a sulfonamide is introduced in the P1 cyclopropyl amino acid, (iii) the position 8 of the quinoline is substituted with a methyl or halo group, and (iv) the ring size of the macrocycle has been reduced to 14 atoms. SAR analysis performed with a limited set of compounds led to the identification of N-{17-[8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2,14-dioxo-3,15-diazatricyclo [13.3.0.0 [Bartenschlager, R.; Lohmann, V. J. Gen. Virol. 2000, 81, 1631; Vincent Soriano, Antonio Madejon, Eugenia Vispo, Pablo Labarga, Javier Garcia-Samaniego, Luz Martin-Carbonero, Julie Sheldon, Marcelle Bottecchia, Paula Tuma, Pablo Barreiro Expert Opin. Emerg. Drugs, 2008, 13, 1-19]]octadec-7-ene-4-carbonyl}(1-methylcyclopropyl)(1-methylcyclopropyl)sulfonamide 19l an extremely potent (Ki = 0.20 nM, EC50 = 3.7 nM), selective, and orally bioavailable dipeptide NS3/4A protease inhibitor, which has features attractive for further preclinical development.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl; R4 is aryl or Het; n is 3, 4, 5, or 6; R5 is halo, C1-6alkyl, hydroxy, C1-6alkoxy, phenyl, or Het; R6 is C1-6alkoxy, or dimethylamino; R7 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R8 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents ; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.