Vonoprazan

Base Information

• Chemical Name: Vonoprazan
• CAS No.: 881681-00-1
• Molecular Formula: C₁₇H₁₆FN₃O₂S
• Molecular Weight: 345.397
• UNII: 1R5L3J156G
• ChEMBL ID: CHEMBL2079130
• DSSTox Substance ID: DTXSID20236869
• Metabolomics Workbench ID: 152845
• NCI Thesaurus Code: C152911
• Nikkaji Number: J2.908.904C
• Pharos Ligand ID: TP9FG29CN411
• RXCUI: 2604577
• Wikidata: Q27887191
• Wikipedia: Vonoprazan
• Mol file: 881681-00-1.mol

Synonyms:Vonoprazan;1-[5-(2-Fluorophenyl)-1-[(pyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl]-N-methylmethanamine;1H-Pyrrole-3-methanamine,5-(2-fluorophenyl)-N-methyl-1-(3-pyridinylsulfonyl);TAK-438 (free base)

Chemical Property of Vonoprazan

Chemical Property:

• Boiling Point: 530.3±60.0 °C(Predicted)
• PKA: 9.06±0.10(Predicted)
• PSA: 72.37000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 4.11730
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 345.09472610
• Heavy Atom Count: 24
• Complexity: 511

Purity/Quality:

99%min ^*data from raw suppliers

Vonoprazan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CNCC1=CN(C(=C1)C2=CC=CC=C2F)S(=O)(=O)C3=CN=CC=C3
• Recent ClinicalTrials: A Study to Determine the Bioavailability of Vonoprazan Sprinkle Capsules on Pudding or on Applesauce Relative to a Vonoprazan Tablet in Healthy Participants
• Recent EU Clinical Trials: A Phase 3 Randomized Multicenter Study to Evaluate the Efficacy and Safety of Open-Label Dual Therapy with Oral Vonoprazan 20 mg or Double-Blind Triple Therapy with Oral Vonoprazan 20 mg Compared to Double-Blind Triple Therapy with Oral Lansoprazole 30 mg Daily in Patients with Helicobacter Pylori Infection
• Recent NIPH Clinical Trials: Gastric microbiota eradication for intestinal metaplasia

Technology Process of Vonoprazan

There total 37 articles about Vonoprazan 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: 86.0%

((5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamic acid tert-butyl ester → 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-yl)-N-methylmethanamine (881681-00-1)

Guidance literature:

With sodium carbonate; trifluoroacetic acid; In dichloromethane; at 25 - 30 ℃; pH=8 - 9; Temperature;

Reference yield: 84.9%

Pyridine-3-sulfonyl chloride (16133-25-8) + 5-(2-fluorophenyl)-1H-pyrrole-3-carboxaldehyde (881674-56-2) + methylamine (74-89-5) → 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-yl)-N-methylmethanamine (881681-00-1)

Guidance literature:

Pyridine-3-sulfonyl chloride; 5-(2-fluorophenyl)-1H-pyrrole-3-carboxaldehyde; With tetrabutylammomium bromide; potassium hydroxide; In N,N-dimethyl-formamide; at 50 - 55 ℃;

methylamine; With sodium tetrahydroborate; In ethanol; N,N-dimethyl-formamide; at 20 ℃; Solvent; Reagent/catalyst;

Reference yield: 80.2%

5‐(2-fluorophenyl)‐1‐(pyridine-3-sulfonyl)-1H-pyrrole-3-carbaldehyde (881677-11-8) + methylamine (74-89-5) → 1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-yl)-N-methylmethanamine (881681-00-1)

Guidance literature:

5‐(2-fluorophenyl)‐1‐(pyridine-3-sulfonyl)-1H-pyrrole-3-carbaldehyde; methylamine; In methanol; at 20 - 30 ℃; for 0.5h; Inert atmosphere;

With sodium tetrahydroborate; In methanol; N,N-dimethyl acetamide; at 0 - 5 ℃; for 1h;

upstream raw materials:

5‐(2-fluorophenyl)‐1‐(pyridine-3-sulfonyl)-1H-pyrrole-3-carbaldehyde

methylamine

ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate

5-(2-fluorophenyl)-1H-pyrrole-3-carboxylic acid ethyl ester

Refernces

• 1、 -. "Preparation method of funolasan fumarate". . . Retrieved 2022/01/10.
• 2、 -. "Vonoprazan salt as well as preparation method and application thereof". Paragraph 0050; 0055-0060. . Retrieved 2021/05/26.