2-((2,4-dichlorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide

Base Information

• Chemical Name: 2-((2,4-dichlorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide
• CAS No.: 666260-75-9
• Deprecated CAS: 956013-38-0
• Molecular Formula: C18H17Cl2F3N4O2
• Molecular Weight: 449.25400
• UNII: VL1I6P2DZ8
• DSSTox Substance ID: DTXSID60216786
• Wikipedia: GW-842,166X
• Wikidata: Q5514863
• Pharos Ligand ID: HPKDQL66ARB2
• Metabolomics Workbench ID: 152984
• ChEMBL ID: CHEMBL225411
• Mol file: 666260-75-9.mol

Synonyms:2-((2,4-dichlorphenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-4-(trifluoromethyl)-5-pyrimidinecarboxamide;GW 842166X;GW-842166X;GW842166X

Chemical Property of 2-((2,4-dichlorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide

Chemical Property:

• PSA: 76.14000
• LogP: 5.16610
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 448.0680657
• Heavy Atom Count: 29
• Complexity: 552

Purity/Quality:

98%Min ^*data from raw suppliers

GW-842166X ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCC1CNC(=O)C2=CN=C(N=C2C(F)(F)F)NC3=C(C=C(C=C3)Cl)Cl
• Recent ClinicalTrials: An Imaging Study to Investigate the Distribution of GW842166X in the Brain.
• Recent EU Clinical Trials: A double-blind, two-period, placebo controlled cross-over study of the effects of the CB2 agonist GW842166 on pain and sensitisation in patients with osteoarthritis.
• Description: The peripheral cannabinoid (CB2) receptor is a G protein-coupled receptor (GPCR) that is localized predominantly in immune cells, monocytes, macrophages, and in several peripheral organs and binds the active component of cannabis, Δ9-tetrahydrocannabinol, as well as anandamide, an endogenous CB receptor ligand. GW 842166X is a peripheral cannabinoid (CB2) receptor agonist with ED50 values of 91 and 63 nM in rat and human, respectively. When administered orally to rats in the Freund’s complete adjuvant (FCA) model of inflammatory pain, GW 842166X is highly potent with an ED50 value of 0.1 mg/kg and full reversal of hyperalgesia at 0.3 mg/kg.
• Uses: GW-842166X is pyrimidine ester based compound that is known as a highly selective CB2 receptor agonist for the treatment of inflammatory and neuropathic pain.

Technology Process of 2-((2,4-dichlorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide

There total 5 articles about 2-((2,4-dichlorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide 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:

methyl 2-chloro-4-(trifluoromethyl)pyrimidine 5-carboxylate (175137-27-6) → 2-(2,4-dichloroanilino)-N-(tetrahydropyran-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide (666260-75-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 358 mg / dioxane / 7 h / Heating

2: 262 mg / KOH / ethanol / 24 h / Heating

3: 34 mg / N-ethylmorpholine; 1-hydroxybenzotriazole hydrate; 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide

With N-ethylmorpholine;; potassium hydroxide; 1-hydroxybenzotriazol-hydrate; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm061195+

Reference yield:

methyl 2-(2,4-dichlorophenyl-amino)-4-trifluoromethyl-pyrimidine-5-carboxylate (666260-76-0) → 2-(2,4-dichloroanilino)-N-(tetrahydropyran-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide (666260-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 262 mg / KOH / ethanol / 24 h / Heating

2: 34 mg / N-ethylmorpholine; 1-hydroxybenzotriazole hydrate; 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide

With N-ethylmorpholine;; potassium hydroxide; 1-hydroxybenzotriazol-hydrate; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm061195+

Reference yield:

2,4-Dichloroaniline (554-00-7,51908-09-9) → 2-(2,4-dichloroanilino)-N-(tetrahydropyran-4-ylmethyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide (666260-75-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 358 mg / dioxane / 7 h / Heating

2: 262 mg / KOH / ethanol / 24 h / Heating

3: 34 mg / N-ethylmorpholine; 1-hydroxybenzotriazole hydrate; 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide

With N-ethylmorpholine;; potassium hydroxide; 1-hydroxybenzotriazol-hydrate; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm061195+

upstream raw materials:

4-tetrahydropyranmethylamine

2-(2,4-dichlorophenylamino)-4-trifluoromethyl-pyrimidine-5-carboxylic acid

methyl 2-chloro-4-(trifluoromethyl)pyrimidine 5-carboxylate

methyl 2-(2,4-dichlorophenyl-amino)-4-trifluoromethyl-pyrimidine-5-carboxylate

Refernces

• 1、 -. "COMBINATION OF CB2 MODULATORS AND PDE4 INHIBITORS FOR USE IN MEDICINE". Page/Page column 53; 54; 55. . Retrieved 2010/02/13.