5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

Base Information

• Chemical Name: 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid
• CAS No.: 162758-35-2
• Molecular Formula: C17H11Cl3N2O2
• Molecular Weight: 381.646
• Hs Code.: 29339900
• UNII: 9Q6ZA9Y42R
• DSSTox Substance ID: DTXSID60364034
• Nikkaji Number: J2.576.010G
• Wikidata: Q72456731
• ChEMBL ID: CHEMBL3589400
• Mol file: 162758-35-2.mol

Synonyms:162758-35-2;5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid;Rimonabant Carboxylic Acid;5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid;1H-Pyrazole-3-carboxylic acid, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-;9Q6ZA9Y42R;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylicacid;183232-62-4;1-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-4-methyl-1h-pyrazole-3-carboxylic acid;5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carboxylic Acid;UNII-9Q6ZA9Y42R;5-(4-chlorophenyl)-1-(;SCHEMBL924033;CHEMBL3589400;DTXSID60364034;MFCD06411080;AKOS015850250;GS-3386;A3622;CS-0143479;FT-0643574;EN300-6746770;Z1741969574;N-(4-tert-Butylsulfanylpyridin-3-yl)-2,2-dimethylpropionamide;1-(2,4-Dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid;5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic ac;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carb oxylic acid;5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3carboxylic acid;5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid;RIMONABANT CARBOXYLIC ACID

Chemical Property of 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 5.52E-13mmHg at 25°C
• Melting Point: 202-203 °C
• Refractive Index: 1.663
• Boiling Point: 551.208 °C at 760 mmHg
• PKA: 3.33±0.34(Predicted)
• Flash Point: 287.161 °C
• PSA: 55.12000
• Density: 1.48 g/cm³
• LogP: 5.50610
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 379.988611
• Heavy Atom Count: 24
• Complexity: 459

Purity/Quality:

99% ^*data from raw suppliers

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi,Xn,T
• Hazard Codes: F,Xi,Xn,T
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N(N=C1C(=O)O)C2=C(C=C(C=C2)Cl)Cl)C3=CC=C(C=C3)Cl
• Uses: 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic Acid is used in the preparation of biarylpyrazole based derivatives as cannabinoid CB1 receptor antagonists. It is metabolite M9 of Rimonabant (R517800), an antiobesity agent. 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic Acid is used in the preparation of biarylpyrazole based derivatives as cannabinoid CB1 receptor antagonists. It is metabolite M9 of Rimonabant (R517800), an antiobesity agent.

Technology Process of 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

There total 33 articles about 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate (158941-22-1) → rimonabant acid (162758-35-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 70 ℃;

DOI:10.1016/j.bmcl.2003.12.068

Reference yield: 96.0%

4-(4-chlorophenyl)-3-methyl-2,4-dioxobutyric acid ethyl ester (169544-41-6) + (2,4-dichlorophenyl)hydrazine (13123-92-7) → rimonabant acid (162758-35-2)

Guidance literature:

4-(4-chlorophenyl)-3-methyl-2,4-dioxobutyric acid ethyl ester; (2,4-dichlorophenyl)hydrazine; In ethanol; for 2.5h; Heating / reflux;

With sodium hydroxide; In ethanol; at 20 ℃; for 2h; Heating / reflux;

Reference yield: 90.0%

4-(4-chlorophenyl)-2-[(2,4-dichlorophenyl)-hydrazono]-3-methyl-4-oxobutyric acid ethyl ester (170937-37-8) → rimonabant acid (162758-35-2)

Guidance literature:

With potassium hydroxide; In ethanol; at 80 ℃; for 3h; Reflux;

DOI:10.1080/00397911.2013.765483

upstream raw materials:

ethyl 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylate

(Z)-ethyl 2-[2-(2,4-dichlorophenyl)hydrazono]-4-(4-chlorophenyl)-3-methyl-4-oxobutanoate

4-(4-chlorophenyl)-3-methyl-2,4-dioxobutyric acid ethyl ester

(2,4-dichlorophenyl)hydrazine

Downstream raw materials:

O 1269

tert-Butyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylate

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(2-methyl-1-morpholinopropan-2-yl)-1H-pyrazole-3-carboxamide

C₂₂H₁₇Cl₃N₄O

Refernces

• 1、 Mishra, Sushanta Kumar,Majumdar, Poulomi,Behera, Rajani Kanta,Behera, Ajaya Kumar. "Synthesis of 3-substituted pyrazole derivatives by mixed anhydride method and study of their antibacterial activities". . p. 32 - 41. Retrieved 2014.
• 2、 -. "MMPL3 INHIBITORS, COMPOSITIONS AND USES THEREOF". Paragraph 0176; 0178. . Retrieved 2020/06/10.
• 3、 -. "Preparation method for rimonabant hydrochloride". Paragraph 0013. . Retrieved 2016/10/17.