Mipitroban

Base Information

• Chemical Name: Mipitroban
• CAS No.: 136122-46-8
• Molecular Formula: C₁₉H₁₉Cl₂N₃O₂
• Molecular Weight: 392.285
• UNII: 2L6Q871829
• DSSTox Substance ID: DTXSID90159672
• Wikidata: Q27254886
• NCI Thesaurus Code: C81462
• Pharos Ligand ID: 364W1L9RDXRV
• ChEMBL ID: CHEMBL18197
• Mol file: 136122-46-8.mol

Synonyms:4-(3-((4-chlorophenyl)methyl)-6-chloroimidazo(4,5-b)pyridin-2-yl)-3,3-dimethylbutanoic acid;UP 116-77;UP-116-77

Chemical Property of Mipitroban

Chemical Property:

• Vapor Pressure: 2.61E-15mmHg at 25°C
• Boiling Point: 601.3°Cat760mmHg
• Flash Point: 317.5°C
• PSA: 68.01000
• Density: 1.35g/cm³
• LogP: 4.82980
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 391.0854322
• Heavy Atom Count: 26
• Complexity: 497

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CC1=NC2=C(N1CC3=CC=C(C=C3)Cl)N=CC(=C2)Cl)CC(=O)O

Technology Process of Mipitroban

There total 7 articles about Mipitroban 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: 75.0%

3,3-dimethylglutaric anhydride (4160-82-1) + 3-amino-5-chloro-2-<(4-chlorophenyl)methyl>aminopyridine (136122-52-6) → β,β-dimethyl-6-chloro-3-((4-chlorophenyl)methyl)-3H-imidazo(4,5-b)pyridine-2-butanoic acid (136122-46-8)

Guidance literature:

With acetic acid; for 8.5h; Heating;

Reference yield:

2,5-dichloro-3-nitropyridine (21427-62-3) → β,β-dimethyl-6-chloro-3-((4-chlorophenyl)methyl)-3H-imidazo(4,5-b)pyridine-2-butanoic acid (136122-46-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium carbonate / 1.) toluene, 30 min, 2.) toluene, from 80 to 85 deg C, 2.5 h

2: 98 percent / H₂, Raney Nickel / methanol / 6.5 h / 15200 Torr

3: 75 percent / acetic acid / 8.5 h / Heating

With hydrogen; nickel; sodium carbonate; acetic acid; In methanol;

Reference yield:

2-<<(4-chlorophenyl)methyl>amino>-3-nitro-5-chloropyridine (136122-48-0) → β,β-dimethyl-6-chloro-3-((4-chlorophenyl)methyl)-3H-imidazo(4,5-b)pyridine-2-butanoic acid (136122-46-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / H₂, Raney Nickel / methanol / 6.5 h / 15200 Torr

2: 75 percent / acetic acid / 8.5 h / Heating

With hydrogen; nickel; acetic acid; In methanol;

upstream raw materials:

3,3-dimethylglutaric anhydride

3-amino-5-chloro-2-<(4-chlorophenyl)methyl>aminopyridine

ethyl 4-<3-<(4-chlorophenyl)methyl>-6-chloroimidazo<4,5-b>pyridin-2-yl>-3,3-dimethylbutanoate

2,5-dichloro-3-nitropyridine

Refernces

• 1、 Nicolai, Eric,Goyard, Joel,Benchetrit, Thierry,Teulon, Jean-Marie,Caussade, Francois,et al.. "Synthesis and Structure - Activity Relationships of Novel Benzimidazole and Imidazopyridine Acid Derivatives as Thromboxane A2 Receptor Antagonists". . p. 1176 - 1187. Retrieved 2007/10/02.