168079-32-1

Basic information

• Product Name: LIXIVAPTAN
• Synonyms: LIXIVAPTAN;N-[3-Chloro-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-5-fluoro-2-methylbenzamide;VPA 985;BenzaMide,N-[3-chloro-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-5-fluoro-2-Methyl-;N-[3-Chloro-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-ylcarbonyl)phenyl]-5-fluoro-2-methylbenzamide;N-[3-chloro-4-(6,11-dihydropyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl)phenyl]-5-fluoro-2-methyl-benzamide
• CAS NO: 168079-32-1
• Molecular Formula: C₂₇H₂₁ClFN₃O₂
• Molecular Weight: 473.933
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 168079-32-1.mol

Chemical Properties

• Boiling Point: 626.5°Cat760mmHg
• Flash Point: 332.7°C
• Appearance: white to beige/
• Density: 1.32
• Vapor Pressure: 1.3E-15mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: room temp
• Solubility: DMSO: soluble20mg/mL, clear
• PKA: 11.86±0.70(Predicted)
• CAS DataBase Reference: LIXIVAPTAN(CAS DataBase Reference)
• NIST Chemistry Reference: LIXIVAPTAN(168079-32-1)
• EPA Substance Registry System: LIXIVAPTAN(168079-32-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 168079-32-1(Hazardous Substances Data)

Usage

Uses

Lixivaptan is a drug used in the treatment and prevention of cardiovascular diseases.

InChI:InChI=1/C27H21ClFN3O2/c1-17-8-9-19(29)13-23(17)26(33)30-20-10-11-22(24(28)14-20)27(34)32-16-21-6-4-12-31(21)15-18-5-2-3-7-25(18)32/h2-14H,15-16H2,1H3,(H,30,33)

Upstream product

• 22162-53-4 10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine 
• 168080-80-6 4-[(5-fluoro-2-methylbenzoyl)amino]-2-chlorobenzoyl chloride 
• 21900-39-0 5-fluoro-2-methylbenzoyl chloride 
• 211040-40-3 2-Chloro-4-(5-fluoro-2-methyl-benzoylamino)-benzoic acid methyl ester 
• 168079-19-4 10,11-Dihydro-10-(2-chloro-4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine 
• 33184-16-6 5-fluoro-2-methylbenzoic acid 
• 22162-51-2 1-(2-Nitrobenzyl)-2-pyrrolecarboxaldehyde 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 1003-29-8 2-pyrrole aldehyde 
• 179063-21-9 (2-chloro-4-nitrophenyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl-methanone 
• 168080-49-7 2-Chloro-4-(5-fluoro-2-methyl-benzoylamino)-benzoic acid 
• 46004-37-9 methyl 4-amino-2-chlorobenzoate 

Downstream Products

• 955402-56-9 C₂₇H₁₉ClFN₃O₃ 
• 955402-80-9 C₂₇H₂₁ClFN₃O₃ 
• 207670-18-6 2-[[10-[2-chloro-4-[(5-fluoro-2-methylbenzoyl)amino]benzoyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]carbonyl]-1,1,1-trimethylhydrazinium iodide 
• 207670-15-3 10-[2-Chloro-4-(5-fluoro-2-methyl-benzoylamino)-benzoyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid,potassium salt 
• 207670-17-5 N-{3-Chloro-4-[3-(N', N'-dimethyl-hydrazinocarbonyl)-5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl]-phenyl}-5-fluoro-2-methyl-benzamide 
• 207670-14-2 10-[2-Chloro-4-(5-fluoro-2-methyl-benzoylamino)-benzoyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid 

Relevant articles and documents

An Improved, Scalable and Impurity-Free Process for Lixivaptan

An optimized synthetic method in high efficiency has been developed for the synthesis of lixivaptan from 2-nitrobenzyl bromide and pyrrole-2-carboxaldehyde. The byproducts among this procedure and an unknown impurity in crude product were investigated. The byproducts were speculated by 1H NMR or MS. The unknown impurity was characterized by 1H NMR, 13C NMR, and HRMS, confirming the structures as N-[3-chloro-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-ylcarbonyl)phenyl]-N-(5-fluoro-2-methylbenzoyl)-5-fluoro-2-methylbenzamide. Afterwards, the impurity was synthesized to make comparisons. The target product lixivaptan was obtained with 47.6% overall yield and 99.93% purity. This cost-effective and environmentally friendly process is suitable for scale-up production.

Tricyclic diazepine vasopressin antagonists and oxytocin antagonists

Tricyclic diazepines of the formula: STR1 wherein A, B, D, E, F, Y and Z are defined in the specification which compounds have vasopressin and oxytocin antagonist activity.