Modipafant

Base Information

• Chemical Name: Modipafant
• CAS No.: 122957-06-6
• Molecular Formula: C₃₄H₂₉ClN₆O₃
• Molecular Weight: 605.096
• UNII: 1DMI0E5023
• DSSTox Substance ID: DTXSID30153811
• Nikkaji Number: J561.816I
• Wikidata: Q27252294
• NCI Thesaurus Code: C90752
• ChEMBL ID: CHEMBL2105829
• Mol file: 122957-06-6.mol

Synonyms:4-(2-chlorophenyl)-6-methyl-2-(4-(2-methylimidazo(4,5-c)pyrid-1-yl)phenyl)-5-(2-pyridinylcarbamoyl)-1,4-dihydropyridine-3-carboxylic acid ethyl ester;modipafant;UK 74505;UK 80067;UK-74505;UK-80067

Chemical Property of Modipafant

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.34g/cm³
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 604.1989665
• Heavy Atom Count: 44
• Complexity: 1120

Purity/Quality:

95% ^*data from raw suppliers

MODIPAFANT 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)NC3=CC=CC=N3)C)C4=CC=C(C=C4)N5C(=NC6=C5C=CN=C6)C
• Isomeric SMILES: CCOC(=O)C1=C(NC(=C([C@H]1C2=CC=CC=C2Cl)C(=O)NC3=CC=CC=N3)C)C4=CC=C(C=C4)N5C(=NC6=C5C=CN=C6)C
• Recent ClinicalTrials: Celgosivir or Modipafant as Treatment for Adult Participants With Uncomplicated Dengue Fever in Singapore

Technology Process of Modipafant

There total 10 articles about Modipafant 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: 31.0%

N-(pyridin-2-yl)-3-aminocrotonamide + 2-chloro-benzaldehyde (89-98-5) + ethyl 4'-(2-methylimidazo[4,5-c]pyridin-1-yl)benzoylacetate (122957-08-8) → (+/-)-Modipafant (122956-68-7,122957-06-6)

Guidance literature:

In ethanol;

Reference yield: 31.0%

2-chloro-benzaldehyde (89-98-5) + N-(2-pyridyl)-3-aminocrotonamide (60155-47-7) + ethyl 4'-(2-methylimidazo[4,5-c]pyridin-1-yl)benzoylacetate (122957-08-8) → (+/-)-Modipafant (122956-68-7,122957-06-6)

Guidance literature:

In ethanol; for 8h; Heating;

DOI:10.1021/jm00095a005

Reference yield:

4-chloro-3-nitropyridine (13091-23-1) → (+/-)-Modipafant (122956-68-7,122957-06-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / ethanol / 18 h / 20 °C

2: 98 percent / H₂ / 10percent Pd/C / methanol; CH₂Cl₂ / 2 h / 20 °C / 1551.4 Torr

3: 81 percent / acetic acid / 2 h / 90 °C

4: 1.) Zn, 2.) 20percent aq. TFA / 1.) THF, reflux, 10 min, 2.) CH₂Cl₂, RT, 15 min

5: 31 percent / ethanol / 8 h / Heating

With hydrogen; trifluoroacetic acid; zinc; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid;

DOI:10.1021/jm00095a005

upstream raw materials:

2-chloro-benzaldehyde

N-(2-pyridyl)-3-aminocrotonamide

ethyl 4'-(2-methylimidazo[4,5-c]pyridin-1-yl)benzoylacetate

3,4-diaminopyridine

Refernces

• 1、 -. "4-Aryl-5-carbamoyl-1,4-dihydropyridines". . . Retrieved 2008/06/13.