193686-76-9

Usage

Uses

Used in Pharmaceutical Industry:
7-Chloro-1,2,3,4-tetrahydro-1-[(4-methylphenyl)sulfonyl]-5H-1-benzazepin-5-one is used as a reactant in the asymmetric preparation of an intermediate in the synthesis of both enantiomers of Tolvaptan (T536650). Tolvaptan is a medication used to treat autosomal dominant polycystic kidney disease (ADPKD) and heart failure. The compound's role in the synthesis process is crucial for producing the desired pharmaceutical product with the correct stereochemistry, ensuring the therapeutic efficacy and safety of the final drug.

InChI:InChI=1/C17H16ClNO3S/c1-12-4-7-14(8-5-12)23(21,22)19-10-2-3-17(20)15-11-13(18)6-9-16(15)19/h4-9,11H,2-3,10H2,1H3

Upstream product

• 247237-43-0 methyl 5-chloro-2-[N-(3-ethoxycarbonyl)propyl-N-p-toluenesulfonyl]aminobenzoate 
• 313673-93-7 7-chloro-1-toluenesulfonyl-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 1133419-00-7 ethyl 7-chloro-5-oxo-1-p-toluenesulfonyl-2,3,4,5-tetrahydro-1H-1-benzazepine-4-carboxylate 
• 247237-38-3 N-p-toluenesulfonyl-5-chloro-anthranilic acid methyl ester 
• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 51282-49-6 methyl 5-chloro-2-nitrobenzoate 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 

Downstream Products

• 160129-45-3 7-chloro-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one 
• 193686-73-6 (S)-7-chloro-5-hydroxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-09-8 7-chloro-5-methoxymethoxy-1-(p-toluenesulfonyl)-2,3-dihydro-1H-1-benzazepine 
• 926035-15-6 (4R,5S)-7-chloro-5-methoxymethoxy-4-(p-nitrobenzoyloxy)-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-16-7 (4S,5R)-7-chloro-4-hydroxy-5-methoxymethoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-17-8 (4R,5S)-7-chloro-4-hydroxy-5-methoxymethoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-18-9 (4R,5R)-4,5-bis(methoxymethoxy)-7-chloro-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-19-0 (4S,5S)-4,5-bis(methoxymethoxy)-7-chloro-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-20-3 (4S,5R)-4,5-bis(methoxymethoxy)-7-chloro-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-21-4 (4R,5S)-4,5-bis(methoxymethoxy)-7-chloro-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-30-5 (4R,5R)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-31-6 (4S,5S)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-32-7 (4S,5R)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 926035-33-8 (4R,5S)-4,5-bis(methoxymethoxy)-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine 

Relevant academic research and scientific papers

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.

Sequential aza-Claisen rearrangement and ring-closing metathesis as a route to 1-benzazepine derivatives

A synthetic strategy based on sequential application of aza-Claisen rearrangement and ring-closing metathesis reaction as key steps has been developed for the synthesis of various 1-benzazepine derivatives of pharmaceutical relevance. Georg Thieme Verlag

7-Chloro-5-hydroxy-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5- tetrahydro-1H-1-benzazepine (OPC-41061): A potent, orally active nonpeptide arginine vasopressin V2 receptor antagonist

We previously reported a series of benzazepine derivatives as orally active nonpeptide arginine vasopressin (AVP) V2 receptor antagonists. After the lead structure OPC-31260 was structurally evaluated and optimized, the introduction of the 7-Cl moiety on the benzazepine and 2-CH3 on the aminobenzoyl moiety enhanced its oral activity. The new AVP-V2 selective antagonist OPC-41061 was determined to be a potent and orally active agent. Copyright (C) 1999 Elsevier Science Ltd.