(2,3-dichlorophenyl)(5-methoxy-2-methyl-3-(2-morpholinoethyl)-1H-indol-1-yl)methanone

Base Information

• Chemical Name: (2,3-dichlorophenyl)(5-methoxy-2-methyl-3-(2-morpholinoethyl)-1H-indol-1-yl)methanone
• CAS No.: 180002-83-9
• Molecular Formula: C₂₃H₂₄Cl₂N₂O₃
• Molecular Weight: 447.361
• Hs Code.: 2934999090
• European Community (EC) Number: 634-036-9
• UNII: 85K154W99L
• DSSTox Substance ID: DTXSID20432728
• Nikkaji Number: J2.981.899A
• Wikipedia: GW-405,833
• Wikidata: Q5514865
• Pharos Ligand ID: 2UDZMZ8FMRHY
• ChEMBL ID: CHEMBL73711
• Mol file: 180002-83-9.mol

Synonyms:1-(2,3-dichlorobenzoyl)-5-methoxy-2-methyl-(2-(mopholin-4-yl)ethyl)-1H-indole;GW405833

Chemical Property of (2,3-dichlorophenyl)(5-methoxy-2-methyl-3-(2-morpholinoethyl)-1H-indol-1-yl)methanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 47-49℃
• Refractive Index: 1.622
• Boiling Point: 544.626 °C at 760 mmHg
• Flash Point: 283.18 °C
• PSA: 43.70000
• Density: 1.326 g/cm³
• LogP: 4.76620
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO at 10-15mg/ml. Also soluble in ethanol at ~5mg/m
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 446.1163980
• Heavy Atom Count: 30
• Complexity: 589

Purity/Quality:

97% ^*data from raw suppliers

1-(2,3-Dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(N1C(=O)C3=C(C(=CC=C3)Cl)Cl)C=CC(=C2)OC)CCN4CCOCC4
• Uses: It is a potent and selective CB2 receptor partial agonist (EC50 = 0.65 nM; maximum inhibition = 44.6%). Binds with high affinity to both human and rat CB2 receptors and displays ~ 1200-fold selectivity over CB1 (Ki values are 3.92 and 4772 nM for human recombinant CB2 and CB1 receptors respectively). Produces potent antihyperalgesic effects in several rodent models of pain.

Technology Process of (2,3-dichlorophenyl)(5-methoxy-2-methyl-3-(2-morpholinoethyl)-1H-indol-1-yl)methanone

There total 3 articles about (2,3-dichlorophenyl)(5-methoxy-2-methyl-3-(2-morpholinoethyl)-1H-indol-1-yl)methanone 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:

2,3-dichlorobenzoyl chloride (2905-60-4) + 4-(2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl)morpholine (180002-82-8) → 1-(2,3-dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole (180002-83-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane; Multistep reaction; 1.) THF;

DOI:10.1016/0960-894X(96)00426-X

Reference yield:

N-(2-chlorethyl)morpholine (3240-94-6) → 1-(2,3-dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole (180002-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) MeMgCl, ZnCl₂ / 1.) Et₂O

2: 1.) KHMDS, HMPA / 1.) THF

With N,N,N,N,N,N-hexamethylphosphoric triamide; methylmagnesium chloride; potassium hexamethylsilazane; zinc(II) chloride;

DOI:10.1016/0960-894X(96)00426-X

Reference yield:

5-methoxy-2-methyl-1H-indole (1076-74-0) → 1-(2,3-dichlorobenzoyl)-5-methoxy-2-methyl-3-[2-(4-morpholinyl)ethyl]-1H-indole (180002-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) MeMgCl, ZnCl₂ / 1.) Et₂O

2: 1.) KHMDS, HMPA / 1.) THF

With N,N,N,N,N,N-hexamethylphosphoric triamide; methylmagnesium chloride; potassium hexamethylsilazane; zinc(II) chloride;

DOI:10.1016/0960-894X(96)00426-X

upstream raw materials:

2,3-dichlorobenzoyl chloride

4-(2-(5-methoxy-2-methyl-1H-indol-3-yl)ethyl)morpholine

N-(2-chlorethyl)morpholine

5-methoxy-2-methyl-1H-indole

Refernces

• 1、 -. "Indole derivatives with affinity for the cannabinoid receptor". . . Retrieved 2008/06/13.