Tezampanel

Base Information

• Chemical Name: Tezampanel
• CAS No.: 154652-83-2
• Deprecated CAS: 150131-78-5
• Molecular Formula: C₁₃H₂₁N₅O₂
• Molecular Weight: 279.342
• UNII: GA36S2O9C2
• Nikkaji Number: J619.679I
• Wikipedia: Tezampanel
• Wikidata: Q7708612
• NCI Thesaurus Code: C80379
• Pharos Ligand ID: FR1DJX1K5A2S
• Metabolomics Workbench ID: 149748
• ChEMBL ID: CHEMBL14935
• Mol file: 154652-83-2.mol

Synonyms:(3S,4aR,6R,8aR)-6-(2-(1(2)H-tetrazole-5yl)ethyl)decahydroisoquinoline-3carboxylic acid;6-(2-(1H-tetrazol-5-yl)ethyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylic acid;LY 215490;LY 293558;LY 326325;LY-215490;LY-293558;LY-326325;LY293558;NGX424;tezampanel

Chemical Property of Tezampanel

Chemical Property:

• Boiling Point: 527.3°Cat760mmHg
• PKA: 2.46±0.40(Predicted)
• Flash Point: 272.7°C
• PSA: 103.79000
• Density: 1.252g/cm³
• LogP: 0.94010
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 279.16952493
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

98%Min ^*data from raw suppliers

LY-293558 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CNC(CC2CC1CCC3=NNN=N3)C(=O)O
• Isomeric SMILES: C1C[C@H]2CN[C@@H](C[C@H]2C[C@H]1CCC3=NNN=N3)C(=O)O
• Recent ClinicalTrials: Study to Assess the Safety, Tolerance and Efficacy of Tezampanel in Patients With Acute Migraine

Technology Process of Tezampanel

There total 11 articles about Tezampanel 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:

ethyl (3S,4aR,8aR)-6-oxo-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate → (3S,4aR,6R,8aR)-6-[2-(1H-tatrazol-5-yl)ethyl]decahydroisoquinoline-3-carboxylic acid (154652-83-2,150131-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / NaN(SiMe₃)2 / tetrahydrofuran

2: 1.) BH₃*SMe₂, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C

With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide; sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1080/10426509608545152

Reference yield:

Ethyl (3S,4aR,8aR)-6-methylidene-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate (157006-68-3) → (3S,4aR,6R,8aR)-6-[2-(1H-tatrazol-5-yl)ethyl]decahydroisoquinoline-3-carboxylic acid (154652-83-2,150131-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) BH₃*SMe₂, 2.) NaOH, H₂O₂ / 1.) THF, 0 deg C

With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide;

DOI:10.1080/10426509608545152

Reference yield:

Ethyl (3S,4aR,6S,8aR)-6-(hydroxymethyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate (157006-69-4) → (3S,4aR,6R,8aR)-6-[2-(1H-tatrazol-5-yl)ethyl]decahydroisoquinoline-3-carboxylic acid (154652-83-2,150131-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) DMSO, oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) -78 deg C, 45 min

2: NaH / tetrahydrofuran / 1.) r.t., 30 min, 2.) 0 deg C, 45 min

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo00104a051

upstream raw materials:

Ethyl (3S,4aR,6S,8aR)-6-(2-cyanoethenyl)-2-carbomethoxy-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

methanol

diethyl 1-cyanomethylphosphonate

Ethyl (3S,4aR,6S,8aR)-6-(hydroxymethyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

Refernces

• 1、 Ornstein, Paul L.,Augenstein, Nancy K.,Arnold, M. Brian. "Stereoselective Synthesis of 6-Substituted Decahydroisoquinoline-3-carboxylates: Intermediates for the Preparation of Conformationally Constrained Acidic Amino Acids". . p. 7862 - 7869. Retrieved 2007/10/02.