Acumapimod

Base Information

• Chemical Name: Acumapimod
• CAS No.: 836683-15-9
• Molecular Formula: C₂₂H₁₉N₅O₂
• Molecular Weight: 385.425
• Hs Code.: 2934999090
• UNII: 2F16KW647L
• Metabolomics Workbench ID: 155500
• NCI Thesaurus Code: C166567
• Pharos Ligand ID: 2NQZLS9FH6WZ
• Wikidata: Q27074309
• Mol file: 836683-15-9.mol

Synonyms:3-(5-Amino-4-(3-cyanobenzoyl)-1H-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamide;acumapimod;Benzamide, 3-(5-amino-4-(3-cyanobenzoyl)-1H-pyrazol-1-yl)-N-cyclopropyl-4-methyl-

Chemical Property of Acumapimod

Chemical Property:

• PSA: 113.80000
• LogP: 3.72988
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 385.15387487
• Heavy Atom Count: 29
• Complexity: 684

Purity/Quality:

98% min ^*data from raw suppliers

Acumapimod(BCT197) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)C(=O)NC2CC2)N3C(=C(C=N3)C(=O)C4=CC=CC(=C4)C#N)N
• Recent ClinicalTrials: Safety & Efficacy of BCT197A2201 in COPD Patients Presenting With an Exacerbation
• Recent EU Clinical Trials: A Phase IIa, two-part, randomised, multi-centre, multinational, double-blind, placebo-controlled, parallel group study to compare the efficacy and safety of BCT197 when added on to standard of care for the treatment of acute respiratory exacerbations of chronic obstructive pulmonary disease (COPD) requiring hospitalisation in adults.

Technology Process of Acumapimod

There total 4 articles about Acumapimod 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: 91.0%

3-[5-amino-4-(3-cyanobenzoyl)-1H-pyrazol-1-yl]-4-methylbenzoic acid + Cyclopropylamine (765-30-0) → 3-[5-amino-4-(3-cyanobenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide (836683-15-9)

Guidance literature:

3-[5-amino-4-(3-cyanobenzoyl)-1H-pyrazol-1-yl]-4-methylbenzoic acid; With 1,1'-carbonyldiimidazole; In dimethyl sulfoxide; at 40 ℃; for 1h;

Cyclopropylamine; In dimethyl sulfoxide; at 40 ℃; for 1h;

Reference yield: 34.0%

3-[5-amino-4-(3-iodo-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide (836682-66-7) → 3-[5-amino-4-(3-cyanobenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide (836683-15-9)

Guidance literature:

With copper(I) cyanide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In DMF (N,N-dimethyl-formamide); at 80 - 100 ℃; for 1h;

Reference yield:

3-(2-cyanoacetyl)benzonitrile (21667-63-0) → 3-[5-amino-4-(3-cyanobenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide (836683-15-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic anhydride / toluene / 1 h / 105 °C / 600.06 - 675.07 Torr

2.1: dimethyl sulfoxide / 2.5 h / 105 °C

3.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 1 h / 40 °C

3.2: 1 h / 40 °C

With acetic anhydride; 1,1'-carbonyldiimidazole; In dimethyl sulfoxide; toluene;

upstream raw materials:

3-[5-amino-4-(3-iodo-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide

Cyclopropylamine

3-(2-cyanoacetyl)benzonitrile

3-amino-p-toluic acid

Refernces

• 1、 -. "SYNTHETIC METHODFOR THE PREPARATION OF AN ALKOXYMETHYLENE-BENZOYLACETONITRILE". Page/Page column 22; 23. . Retrieved 2020/05/12.
• 2、 -. "5-MEMBERED HETEROCYCLE-BASED P38 KINASE INHIBITORS". Page/Page column 110; 135. . Retrieved 2010/02/10.