Mozavaptan

Base Information

• Chemical Name: Mozavaptan
• CAS No.: 137975-06-5
• Molecular Formula: C27H29N3O2
• Molecular Weight: 427.546
• UNII: 17OJ42922Y
• DSSTox Substance ID: DTXSID8057641
• Nikkaji Number: J464.170A
• Wikipedia: Mozavaptan
• Wikidata: Q12746116
• NCI Thesaurus Code: C77018
• Pharos Ligand ID: UZ13PXG9QUVJ
• ChEMBL ID: CHEMBL420762
• Mol file: 137975-06-5.mol

Synonyms:5-dimethylamino-1-(4-(2-methylbenzoylamino)benzoyl)-2,3,4,5-tetrahydro-1H-benzazepine;benzamide, N-(4-((5-(dimethylamino)-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl)phenyl)-2-methyl-, hydrochloride (1:1);mozavaptan;mozavaptan hydrochloride;mozavaptane hydrochloride;N-(4-(((5RS)-5-(dimethylamino)-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl)phenyl)-2-methylbenzamide;OPC 31260;OPC-31260;physuline

Chemical Property of Mozavaptan

Chemical Property:

• Vapor Pressure: 7.49E-12mmHg at 25°C
• Refractive Index: 1.646
• Boiling Point: 543 °C at 760 mmHg
• Flash Point: 282.2 °C
• PSA: 52.65000
• Density: 1.21 g/cm³
• LogP: 5.42860
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 427.22597718
• Heavy Atom Count: 32
• Complexity: 643

Purity/Quality:

99% ^*data from raw suppliers

Mozavaptan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C(=O)NC2=CC=C(C=C2)C(=O)N3CCCC(C4=CC=CC=C43)N(C)C
• Description: Mozavaptan is an oral vasopressin V2 antagonist that has been launched in Japan for inappropriate antidiuretic hormone secretion syndrome (IADHS), an affliction manifesting as hyponatremia. It joins another nonpeptidic benzazepine, conivaptan, which corrects sodium and water imbalance by blocking the renal V2 receptor resulting in enhanced diuresis, thereby effectively increasing serum sodium concentration. While conivaptan inhibits both V1 and V2 receptors, mozavaptan is significantly more selective for V2 (IC50 of 14nM vs. 1.2 mM for V1).
• Uses: vasopressin V2 receptor antagonist Mozavaptan is a vasopressin-receptor antagonist. It is used in the treatment of congestive heart failure and hyponatremia.

Technology Process of Mozavaptan

There total 6 articles about Mozavaptan 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: 54.0%

ortho-toluoyl chloride (933-88-0) + 5-dimethylamino-1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzoazepine (165309-37-5) → mozavaptan (137975-06-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 5 ℃; for 0.5h;

DOI:10.1021/jm960133o

Reference yield: 35.0%

C27H29N3O3 → 5-methylamino-1-[4-[(2-methylbenzoyl)amino]benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (154890-02-5) + mozavaptan (137975-06-5)

Guidance literature:

With 1H-imidazole; 5,10,15,20-tetraphenyl-21 H,23-H-porphine manganese(III)chloride; In dichloromethane; at 20 ℃;

DOI:10.3987/com-98-s(h)6

Reference yield:

4-nitro-benzoyl chloride (122-04-3) → mozavaptan (137975-06-5)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

2: H₂ / 10percent Pd/C / ethanol / 5 h / 760 Torr / Ambient temperature

3: 54 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 - 5 °C

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1021/jm960133o

upstream raw materials:

ortho-toluoyl chloride

5-dimethylamino-1-(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-benzoazepine

4-nitro-benzoyl chloride

5-dimethylamino-2,3,4,5-tetrahydro-1H-benzoazepine

Refernces

• 1、 Ogawa, Hidenori,Yamashita, Hiroshi,Kondo, Kazumi,Yamamura, Yoshitaka,Miyamoto, Hisashi,Kan, Keizo,Kitano, Kazuyoshi,Tanaka, Michinori,Nakaya, Kenji,Nakamura, Shigeki,Mori, Toyoki,Tominaga, Michiaki,Yabuuchi, Youichi. "Orally active, nonpeptide vasopressin V2 receptor antagonists: A novel series of 1-[4-(benzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepines and related compounds". . p. 3547 - 3555. Retrieved 2007/10/03.