N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

Base Information

• Chemical Name: N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide
• CAS No.: 137973-76-3
• Molecular Formula: C26H23ClN2O3
• Molecular Weight: 446.933
• Hs Code.: 2933990090
• UNII: YR22W5RA83
• DSSTox Substance ID: DTXSID60463591
• Nikkaji Number: J1.670.412A
• Wikidata: Q72459678
• Mol file: 137973-76-3.mol

Synonyms:137973-76-3;5-Dehydro Tolvaptan;N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide;N-[4-[(7-CHLORO-2,3,4,5-TETRAHYDRO-5-OXO-1H-1-BENZAZEPIN-1-YL)CARBONYL]-3-METHYLPHENYL]-2-METHYLBENZAMIDE;C26H23ClN2O3;N-[4-(7-chloro-5-oxo-3,4-dihydro-2H-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide;YR22W5RA83;N-(4-((7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl)-3-methylphenyl)-2-methylbenzamide;Benzamide, N-(4-((7-chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl)-3-methylphenyl)-2-methyl-;Benzamide, N-[4-[(7-chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methyl-;N-[4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide;UNII-YR22W5RA83;SCHEMBL533754;DTXSID60463591;VENGMROMZOKURN-UHFFFAOYSA-N;AMY40478;MFCD19440797;AKOS016006852;AC-25521;AS-20018;CS-0138429;FT-0696493;EN300-7421953;J-007084;Z3235029167;5-oxo-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)-benzoyl]-2,3,4,5-tetra-hydro-1H-benzoazepine;5-oxo-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetra-hydro-1H-benzoazepine;5-oxo-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine;7-chloro-1-[2-methyl-4-(2-methyl benzoyl amino) benzoyl]-5 oxo-2,3,4,5-tetrahydro-1H-1-benzazepine;7-chloro-1-[2-methyl-4-(2-methylbenzoyl-amino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one;7-chloro-1-[2-methyl-4-(2-methylbenzoylamino) benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine;7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one;7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine

Chemical Property of N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

Chemical Property:

• Boiling Point: 593.224 °C at 760 mmHg
• PKA: 12.97±0.70(Predicted)
• Flash Point: 312.571 °C
• PSA: 66.48000
• Density: 1.307 g/cm³
• LogP: 5.97040
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 446.1397203
• Heavy Atom Count: 32
• Complexity: 713

Purity/Quality:

99% ^*data from raw suppliers

5-DehydroTolvaptan ^*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(=O)C4=C3C=CC(=C4)Cl)C
• Uses: 5-Dehydro Tolvaptan is an impurity of Tolvaptan (T536650), a selective, competitive arginine vasopressin V2 receptor antagonist ngestive heart failure, cirrhosis, and the syndrome of inappropriate antidiuretic hormone (SIADH). 5-Dehydro Tolvaptan is an impurity of Tolvaptan (T536650), a selective, competitive arginine vasopressin V2 receptor antagonist used to treat hyponatremia (low blood sodium levels) associated with congestive heart failure, cirrhosis, and the syndrome of inappropriate antidiuretic hormone (SIADH g

Technology Process of N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

There total 31 articles about N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide 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: 96.0%

ortho-toluoyl chloride (933-88-0) + 1-(4-amino-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine (137977-97-0) → MOP-21826 (137973-76-3)

Guidance literature:

1-(4-amino-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine; With magnesium hydroxide; In dichloromethane; water; at 10 ℃; for 0.5h;

ortho-toluoyl chloride; In dichloromethane; water; for 3h;

Reference yield: 90.4%

tolvaptan (150683-30-0) → MOP-21826 (137973-76-3)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; Reflux;

Reference yield: 85.0%

carbon monoxide (201230-82-2) + 7-chloro-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one (160129-45-3) + 2-bromo-5-(2-methylbenzoylamino)toluene (317374-07-5) → MOP-21826 (137973-76-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium diacetate; In N,N-dimethyl-formamide; at 125 ℃; for 3h;

DOI:10.1016/j.bmcl.2007.09.094

upstream raw materials:

ortho-toluoyl chloride

1-(4-amino-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine

carbon monoxide

7-chloro-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one

Downstream raw materials:

N-(4-(7-chloro-5-hydroxy-2,3,4-trihydro-5-deutero-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

(-)-Tolvaptan

(+)-Tolvaptan

tolvaptan

Refernces

• 1、 Torisawa, Yasuhiro,Furuta, Takuya,Nishi, Takao,Aki, Shinji,Minamikawa, Jun-ichi. "Aminocarbonylation route to tolvaptan". . p. 6455 - 6458. Retrieved 2007.
• 2、 -. "Preparation method of high-purity tolvaptan". Paragraph 0056-0058. . Retrieved 2021/06/23.
• 3、 -. "IMPROVED METHODS OF PRODUCING SYNTHETIC INTERMEDIATES OF TOLVAPTAN". Paragraph 0029; 0030. . Retrieved 2018/04/07.