137973-76-3

Basic information

• Product Name: N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide
• Synonyms: N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide;7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine;N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbe;5-Dehydro Tolvaptan;N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-Methylphenyl)-2-MethylbenzaMide;Dehydrotolvaptan;N-[4-[7-Chloro-2,3,4,5-Tetrahydro-5-oxo-1H-1-Benzazepine-1-yl)carbonyl]-3-MethylPhenyl]-2-MethylBenzamide;N-[4-(7-chloro-5-oxo-3,4-dihydro-2H-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide
• CAS NO: 137973-76-3
• Molecular Formula: C₂₆H₂₃ClN₂O₃
• Molecular Weight: 446.93
• EINECS: 1312995-182-4
• Product Categories: Tolvaptan intermediate
• Mol File: 137973-76-3.mol

Chemical Properties

• Boiling Point: 593.224 °C at 760 mmHg
• Flash Point: 312.571 °C
• Appearance: /
• Density: 1.307
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.97±0.70(Predicted)
• CAS DataBase Reference: N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide(137973-76-3)
• EPA Substance Registry System: N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide(137973-76-3)

Safety Data

• Hazardous Substances Data: 137973-76-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide is used as an active pharmaceutical ingredient for the treatment of various medical conditions. Its specific application reason is due to its interaction with biological targets, such as receptors or enzymes, which can modulate physiological processes and provide therapeutic benefits.
Used in Chemical Research:
In the field of chemical research, N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide can be used as a starting material or a synthetic intermediate for the development of new compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Drug Synthesis:
N-[4-[(7-Chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepin-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide is used as a key intermediate in the synthesis of various drugs, particularly those targeting the central nervous system or cardiovascular system. Its application reason is based on its structural similarity to known pharmacophores and its potential to be modified to improve drug efficacy, safety, or pharmacokinetic properties.

Upstream product

• 933-88-0 ortho-toluoyl chloride 
• 137977-97-0 1-(4-amino-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 201230-82-2 carbon monoxide 
• 160129-45-3 7-chloro-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one 
• 317374-07-5 2-bromo-5-(2-methylbenzoylamino)toluene 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 30459-70-2 2-methyl-4-nitrobenzoyl chloride 
• 1975-51-5 2-methyl-4-nitrobenzoic acid 
• 51282-49-6 methyl 5-chloro-2-nitrobenzoate 
• 331947-69-4 2-methyl-4-(2-methylbenzoylamino)benzoic acid chloride 
• 317374-08-6 2-methyl-4-(2-methylbenzoylamino)benzoic acid 
• 150683-30-0 tolvaptan 
• 247237-43-0 methyl 5-chloro-2-[N-(3-ethoxycarbonyl)propyl-N-p-toluenesulfonyl]aminobenzoate 

Downstream Products

• 1296212-17-3 N-(4-(7-chloro-5-hydroxy-2,3,4-trihydro-5-deutero-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide 
• 331947-44-5 (-)-Tolvaptan 
• 331947-66-1 (+)-Tolvaptan 
• 150683-30-0 tolvaptan 
• 165310-94-1 5-ethoxy-carbonylmethylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoyl-amino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine 

Relevant articles and documents

Efficient and promising asymmetric preparation of enantiopure tolvaptan via transfer hydrogenation with robust catalysts

Enantiopure tolvaptan, the first and only oral vasopressin antagonist for hyponatremia has been prepared by using an asymmetric transfer hydrogenation as a key step with HCOOH-Et3N or HCOONa-H2O as the hydrogen donor in open air. Good chemical yields with up to 99% enantioselectivity were obtained with a 1000:1 of S/C in an HCOONa-H2O system. The air and water stable catalysts provide a very promising prospect for industrial application.

Aminocarbonylation route to tolvaptan

Pd-catalyzed aminocarbonylation between aryl bromide and NH-benzazepinone was effectively carried out to furnish the key intermediate for tolvaptan (up to 85%) in one step.

INTERMEDIATES AND METHODS FOR THE PREPARATION OF TOLVAPTAN AND ITS DERIVATIVES

The present invention relates to new intermediates for the synthesis of tolvaptan and its derivatives, as well as a method for its preparation involving said intermediates.

Novel benzoazepine compound, composition and applications of novel benzoazepine compound and composition

The invention relates to a novel benzoazepine compound, which comprises a pharmaceutically acceptable salt thereof. The invention also provides a pharmaceutical composition containing the compound and the pharmaceutically acceptable salt thereof. The pres

Preparation method of high-purity tolvaptan

The invention provides a preparation method of high-purity tolvaptan. Specifically, the quality of an intermediate N-(4-(7-chloro-5-oxo-2, 3, 4, 5-tetrahydro-1H-benzo[b]aza-1-ylcarbonyl)-3-methylphenyl)-2-methylbenzamide is controlled through crystallization and purification, so that the high-purity intermediate is obtained, and the high-purity tolvaptan is obtained by controlling the process conditions of reducing the intermediate to obtain the tolvaptan and subsequently purifying the tolvaptan. The method is low in cost, simple in preparation process and mild in reaction condition, the purity of the prepared tolvaptan reaches 99.9% or above, the yield reaches 80% or above, and industrial production is facilitated.

IMPROVED METHODS OF PRODUCING SYNTHETIC INTERMEDIATES OF TOLVAPTAN

PROBLEM TO BE SOLVED: To provide improved methods of producing 7-chloro-1-(2-methyl-4-nitrobenzoyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine. SOLUTION: The present invention provides methods of producing 7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine and 7-chloro-1-(2-methyl-4-nitrobenzoyl)-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine, which are synthetic intermediates of tolvaptan, by condensing an amino group and a carboxyl group in the presence of magnesium hydroxide. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Method for preparing high-purity tolvaptan intermediate

The invention provides a method for preparing a high-purity tolvaptan intermediate, and concretely provides a method for purifying a tolvaptan intermediate N-[4-[(7-chloro-2,3,4,5-tetrahydro-5-oxo-1H-1-benzazepine-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide (formula II). A crude product containing the compound of formula II is recrystallized by an organic solvent composed of ester, haloalkaneand ether to preferably obtain the compound of formula II, having a purity of above 99.00%.

Preparation method of tolvaptan

The invention discloses a preparation method of tolvaptan. According to the preparation method, 7-chloro-1,2,3,4-tetrahydrobenzo[b]azepine-5-one and 4-nitro-2-methyl bromobenzene are taken as the primary raw materials; high purity tolvaptan is obtained after steps of carbonyl inserting reactions, reduction reactions, and acylation reactions, and the yield is high. The preparation method has the advantages that no bromine or tin dichloride is used; the preparation method does not generate a large amount of industrial waste water, and the environment is protected. At the same time, the generation of impurities namely a compound V and a compound VIII is avoided, and the purification becomes easier. No explosive, flammable, and toxic solvent such as chloroform, ether, and the like, is used, the requirements on the protection of workers are lowered, and the safe production is guaranteed. Moreover, the route design is novel, the raw materials are easily available, the operation of the technology is simple and feasible, and a simple and feasible method is provided for the massive industrial production of tolvaptan.

Preparation method of high-efficiency low-toxicity pitressin antagonist

The invention provides a preparation method of a high-efficiency low-toxicity pitressin antagonist. Specifically, the invention provides a compound having the formula A shown in the description, and a method for preparing tolvaptan through the compound having the formula A. All groups in the formula are defined in the description. The method has advantages of environmental protection, available raw materials, and high overall yield, and is suitable for industrial preparation of tolvaptan.

Preparation method for cardiovascular disease treatment drug

The invention provides a preparation method for a cardiovascular disease treatment drug. Specifically, the invention provides a compound represented by a formula (IV) shown in the description and a method for preparing Tolvaptan from the compound represented by the formula (IV). The method provided by the invention has the advantages of being environment-friendly, being easy in raw material obtaining and high in total yield, and the like, thereby being applicable to the industrialized preparation of Tolvaptan.