Tirilazad

Base Information

• Chemical Name: Tirilazad
• CAS No.: 110101-66-1
• Molecular Formula: C₃₈H₅₂N₆O₂
• Molecular Weight: 624.87
• UNII: YD064E883I
• DSSTox Substance ID: DTXSID30869521
• Nikkaji Number: J291.745I
• Wikipedia: Tirilazad
• Wikidata: Q7809222
• NCI Thesaurus Code: C152658
• Metabolomics Workbench ID: 153922
• ChEMBL ID: CHEMBL1630578
• Mol file: 110101-66-1.mol

Synonyms:21-(4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl)-16-methylpregna-1,4,9(11)-triene-3,20-dione monomethane sulfonate;Freedox;pregna-1,4,9(11)-triene-3,20-dione, 21-(4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl)-16-methyl-, (16alpha)-, monomethanesulfonate;tirilazad;tirilazad mesylate;tirilazad mesylate hydrate;U 74006F;U-74006;U-74006F;U74006F

Chemical Property of Tirilazad

Chemical Property:

• Vapor Pressure: 1.71E-26mmHg at 25°C
• Boiling Point: 812.9°Cat760mmHg
• PKA: 12.04±0.50(Predicted)
• Flash Point: 445.4°C
• PSA: 72.88000
• Density: 1.25g/cm³
• LogP: 5.59120
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 624.41517492
• Heavy Atom Count: 46
• Complexity: 1290

Purity/Quality:

98%Min ^*data from raw suppliers

TIRILAZAD 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3=CCC2(C1C(=O)CN5CCN(CC5)C6=NC(=NC(=C6)N7CCCC7)N8CCCC8)C)C
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4(C3=CC[C@@]2([C@H]1C(=O)CN5CCN(CC5)C6=NC(=NC(=C6)N7CCCC7)N8CCCC8)C)C
• Recent ClinicalTrials: Methylprednisolone Given by 24-Hour or 48-Hour Infusion Versus Tirilazad for Acute Spinal Cord Injury

Technology Process of Tirilazad

There total 3 articles about Tirilazad 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:

2,4-di(1-pyrrolidinyl)-6-chloropyrimidine (111669-15-9) → 16α-methyl-21-[4-[2,6-bis(1-pyrrolidinyl)-4-pyrimidinyl]-1-piperazinyl]-pregna-1,4,9(11)-triene-3,20-dione (110101-66-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / pyridine / 50 h / 100 °C

2: NaI, K₂CO₃ / acetonitrile / 42 h / Ambient temperature

With pyridine; potassium carbonate; sodium iodide; In acetonitrile;

DOI:10.1021/jm00166a010

Reference yield:

21-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione (56016-90-1) → 16α-methyl-21-[4-[2,6-bis(1-pyrrolidinyl)-4-pyrimidinyl]-1-piperazinyl]-pregna-1,4,9(11)-triene-3,20-dione (110101-66-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / acetonitrile / 2 h / 0 °C

2: NaI, K₂CO₃ / acetonitrile / 42 h / Ambient temperature

With potassium carbonate; triethylamine; sodium iodide; In acetonitrile;

DOI:10.1021/jm00166a010

Reference yield:

2,4-bis(1-pyrrolidinyl)-6-(1-piperazinyl)-pyrimidine (111641-17-9) + 21-(methanesulphonyloxy)-16α-methylpregna-1,4,9(11)-trien-3,20-dione (197711-91-4) → 16α-methyl-21-[4-[2,6-bis(1-pyrrolidinyl)-4-pyrimidinyl]-1-piperazinyl]-pregna-1,4,9(11)-triene-3,20-dione (110101-66-1)

Guidance literature:

With potassium carbonate; sodium iodide; In acetonitrile; for 42h; Yield given; Ambient temperature;

DOI:10.1021/jm00166a010

upstream raw materials:

2,4-bis(1-pyrrolidinyl)-6-(1-piperazinyl)-pyrimidine

21-(methanesulphonyloxy)-16α-methylpregna-1,4,9(11)-trien-3,20-dione

2,4-di(1-pyrrolidinyl)-6-chloropyrimidine

21-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

Refernces