113206-03-4

Basic information

• Product Name: 2-Chloro-3-methoxyaniline
• Synonyms: Benzenamine, 2-chloro-3-methoxy-;2-Chloro-3-methoxybenzenamine;(2-Chloro-3-methoxyphenyl)amine;2-Chloro-3-methoxyaniline;2-chloro-3-methoxyl-aniline;1,3-ADAMANTANEDIMETHANOL,ALPHA,ALPHA,ALPHA'',ALPHA''-TETRAMETHYL-(6CI);2-chloro-3-Methoxy-;3-AMino-2-chloroanisole[2-Chloro-3-Methoxyaniline]
• CAS NO: 113206-03-4
• Molecular Formula: C₇H₈ClNO
• Molecular Weight: 157.6
• Product Categories: Drug Intermediates;API intermediates;Anilines, Amides & Amines;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds;Naphthyridine,Quinoline
• Mol File: 113206-03-4.mol

Chemical Properties

• Melting Point: 50 °C
• Boiling Point: 252 °C at 760 mmHg
• Flash Point: 106.2 °C
• Appearance: Kind of white to yellow powder
• Density: 1.234 g/cm³
• Vapor Pressure: 0.00191mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.23±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-3-methoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3-methoxyaniline(113206-03-4)
• EPA Substance Registry System: 2-Chloro-3-methoxyaniline(113206-03-4)

Safety Data

• Hazardous Substances Data: 113206-03-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-3-methoxyaniline is used as a reactant for the preparation of dual inhibitors of CK2 and Pim kinases. These inhibitors exhibit antiproliferative activity against cancer cells, making them valuable in the development of novel cancer treatments. The compound plays a crucial role in the synthesis of these inhibitors, contributing to their potential therapeutic effects.

InChI:InChI=1/C7H8ClNO.ClH/c1-10-6-4-2-3-5(9)7(6)8;/h2-4H,9H2,1H3;1H

Upstream product

• 3970-39-6 2-chloro-3-methoxynitrobenzene 
• 1073118-74-7 C₁₂H₁₆ClNO₃ 
• 16554-45-3 2-methoxy-6-nitroaniline 

Downstream Products

• 174913-11-2 3-bromo-2-chloro-anisole 
• 85893-88-5 2-amino-3-chloro-2'-fluoro-4-hydroxybenzophenone 
• 150637-97-1 2-Chloro-3-methoxyacetanilide 
• 923289-36-5 1-(2-amino-3-chloro-4-methoxy-phenyl)ethanone 
• 801281-96-9 C₁₃H₁₄ClNO₅ 
• 1253380-82-3 methyl [[(2-chloro-4-fluorophenyl)methyl](2-{[2-chloro-3-(methyloxy)phenyl]amino}ethyl)amino](oxo)acetate 
• 893620-26-3 2,4,8-trichloro-7-methoxyquinoline 
• 1108659-39-7 2,8-dichloro-7-methoxy-4-(4-methoxybenzyloxy)quinoline 

Relevant articles and documents

Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts

The enantioselective syntheses of axially chiral heterobiaryls were accomplished through the aromatic electrophilic halogenation of 3-(quinolin-8-yl)phenols with bifunctional organocatalysts that control the molecular conformations during successive halogenations. Axially chiral quinoline derivatives, which have rarely been synthesized in an enantioselective catalytic manner, were afforded in moderate-to-good enantioselectivities through bromination, and an analogous protocol also enabled enantioselective iodination. In addition, this catalytic reaction, which allows enantioselective control through the use of mono-ortho-substituted substrates, allowed the asymmetric synthesis of 8-arylquinoline derivatives bearing two different halogen groups in high enantioselectivities.

TRPV4 ANTAGONISTS

The present invention relates to quinoline analogs, pharmaceutical compositions containing them and their use as TRPV4 antagonists.

DIKETOPIPERAZINE DERIVATIVES AS P2X7 MODULATORS

The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof: (I) wherein: A represents an aryl, heteroaryl or heterocyclyl group; and any ring or ring system of said aryl or heteroaryl is optionally substituted with 1 to 3 substituents, which may be the same or different, selected from the group consisting of halogen, C1-6 alkyl, -CF3, - OCF3, cyano, C1-6 alkoxy, -NR10R11, -X-aryl, -X-heteroaryl and -X-heterocyclyl; R1, R2, R3, R4 and R5 independently represent hydrogen, fluorine, chlorine, -CF3, cyano or C1-6 alkyl, such that at least one of R1, R2, R3, R4 and R5 is other than hydrogen; R6, R7, R8, R9, R10 and R11 independently represent hydrogen or C1-6 alkyl; X represents a linker selected from a bond, -(CH2)n- and -O-(CH2)n-; and n represents an integer from 1 to 3. The compounds or salts modulate P2X7 receptor function and are capable of antagonizing the effects of ATP at the P2X7 receptor ("P2X7 receptor antagonists").

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.

HEPATITIS C INHIBITOR DIPEPTIDE ANALOGS

The present invention relates to compounds of formula (I): wherein R1, R2, R4, n and m are as defined herein and R3 is selected from: (i) -C(O)OR31 wherein R31 is (C1-6)alkyl or aryl, wherein the (C1-6)alkyl is optionally substituted with one to three halogen substituents; (ii) -C(O)NR32R33, wherein R32 and R33 are each independently selected form H, (C1-6)alkyl, and Het; (iii) -SOvR34, wherein v is 1 or 2 and R34 is selected from: (C1-6)alkyl, aryl, Het, and NR32R33 wherein R32 and R33 are as defined above; and (iv) -CO(O)-R35, wherein R35 is selected from (C1-8)alkyl, (C3-7)cycloalkyl-(C1-4)alkyl, aryl, aryl-(C1-6)alkyl, Het and Het-(C1-6)alkyl, each of which are optionally substituted with one or more substituents each independently selected from halo, (C1-6)alkyl, (C3-7)cycloalkyl, aryl, Het, hydroxyl, -O-(C1-6)alkyl, -S-(C1-6)alkyl, -SO-(C1-6)alkyl, -SO2-(C1-6)alkyl, -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl, wherein the aryl portion of the -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl are each optionally substituted with one to five halo substituents. The present invention further relates to pharmaceutical compositions containing the compounds of formula (I) and methods for using these analogs in the treatment of HCV infection.

Hepatitis C inhibitor peptide analogs

Compounds of formula (I): wherein R1, R2, R3, R4, R5, Y, n and m are as defined herein. The compounds are useful as inhibitors of HCV NS3 protease.

HEPATITIS C INHIBITOR PEPTIDE ANALOGS

The invention relates to compounds of formula (I) wherein R', R2, R3, R4, R5, R6, Y, n and m are as defined herein. The compounds are useful for the treatment and prevention of hepatitis C viral infections in mammals by inhibiting HCV NS3 protease. The invention further relates to azalactone compounds of the formula (III) which can be reacted with an amide anion to produce the compounds of formula (I).

HEPATITIS C INHIBITOR COMPOUNDS

Compounds of formula (I): wherein B, X, R3, L0, L1, L2, R2, R1 and RC are defined herein. The compounds are useful as inhibitors of HCV NS3 protease for the treatment of hepatitis C viral infection.