5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide

Base Information

• Chemical Name: 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide
• CAS No.: 1272353-82-8
• Molecular Formula: C25H20N6O2S
• Molecular Weight: 468.539
• Mol file: 1272353-82-8.mol

Synonyms:5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide;BMS-919373

Chemical Property of 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide

Chemical Property:

• PSA: 132.13000
• LogP: 5.86740

Purity/Quality:

98% ^*data from raw suppliers

BMS-919373 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: BMS-919373 (CAS# 1272353-82-8) is an intermediate in the synthesis of clinical candidate 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)pyridine-3-sulfonamide as a selective IKur inhibitor for potential treatment of atrial fibrillation.

Technology Process of 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide

There total 23 articles about 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide 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: 82.0%

N-(tert-butyl)-5-(5-phenyl-4-((pyridin-2ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide (1272356-31-6) → 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide (1272353-82-8)

Guidance literature:

With hydrogenchloride; In water; at 80 ℃; for 3h;

DOI:10.1021/acs.joc.8b02254

Reference yield:

pyridine-3-sulfonamide-5-ylboronic acid pinacol ester (1083326-26-4) + 2-chloro-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine (1272353-93-1) → 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide (1272353-82-8)

Guidance literature:

With potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; water; at 90 ℃; for 16h; Inert atmosphere;

Reference yield:

5-bromopyridine-3-sulfonamide (62009-33-0) → 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridine-3-sulfonamide (1272353-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 0.75 h / 120 °C / Inert atmosphere; Microwave irradiation

2: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 16 h / 90 °C / Inert atmosphere

With potassium acetate; potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; water;

upstream raw materials:

phenylboronic acid

5-bromoquinazoline-2,4(1H,3H)-dione

4-bromoisatin

2-amino-6-chlorobenzoic acid

Refernces

• 1、 Gunaga, Prashantha,Lloyd, John,Mummadi, Somanadham,Banerjee, Abhisek,Dhondi, Naveen Kumar,Hennan, James,Subray, Veena,Jayaram, Ramya,Rajugowda, Nagendra,Umamaheshwar Reddy, Kommuri,Kumaraguru, Duraimurugan,Mandal, Umasankar,Beldona, Dasthagiri,Adisechen, Ashok Kumar,Yadav, Navnath,Warrier, Jayakumar,Johnson, James A.,Sale, Harinath,Putlur, Siva Prasad,Saxena, Ajay,Chimalakonda, Anjaneya,Mandlekar, Sandhya,Conder, MaryLee,Xing, Dezhi,Gupta, Arun Kumar,Gupta, Anuradha,Rampulla, Richard,Mathur, Arvind,Levesque, Paul,Wexler, Ruth R.,Finlay, Heather J.. "Selective IKur Inhibitors for the Potential Treatment of Atrial Fibrillation: Optimization of the Phenyl Quinazoline Series Leading to Clinical Candidate 5-[5-Phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl]pyridine-3-sulfonamide". . p. 3795 - 3803. Retrieved 2017/05/19.