BMS-911543

Base Information

• Chemical Name: BMS-911543
• CAS No.: 1271022-90-2
• Molecular Formula: C23H28N8O
• Molecular Weight: 432.52142
• Mol file: 1271022-90-2.mol

Synonyms:N,N-dicyclopropyl-4-((1,5-dimethyl-1H-pyrazol-3-yl)amino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide;

Chemical Property of BMS-911543

Chemical Property:

• PSA: 89.03000
• LogP: 2.91730
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: ≥43.3 mg/mL in DMSO with gentle warming; insoluble in H2O; ≥9.8 mg/mL in EtOH with gentle warming and ultrasonic

Purity/Quality:

99% ^*data from raw suppliers

BMS911543 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: BMS 911543 is a functionally selective small molecule inhibitor of JAK2 and have been developed as a treatment for leukemia.

Technology Process of BMS-911543

There total 40 articles about BMS-911543 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: 89.0%

sodium 4-((1,5-dimethyl-1H-pyrazol-3-yl)amino)-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxylate + N-cyclopropylcyclopropanamine hydrochloride (246257-69-2) → BMS-911543 (1271022-90-2)

Guidance literature:

With 2-chloro-1,3-dimethylimidazolinium chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 - 25 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.5b00572

Reference yield: 63.9%

(Z)-N,N-dicyclopropyl-6-ethyl-1-methyl-4-(1-(methylthio)-3-oxobut-1-enylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (1271025-08-1) + 1-methyl-1-tert-butoxycarbonylhydrazine (21075-83-2) → BMS-911543 (1271022-90-2)

Guidance literature:

(Z)-N,N-dicyclopropyl-6-ethyl-1-methyl-4-(1-(methylthio)-3-oxobut-1-enylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide; 1-methyl-1-tert-butoxycarbonylhydrazine; With acetic acid; at 35 ℃; for 4h;

With formic acid; at 60 ℃; for 6h;

Reference yield: 31.7%

4-iodo-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (1271025-10-5) + 1,5-dimethyl-1H-pyrazol-3-ylamine (35100-92-6) → BMS-911543 (1271022-90-2)

Guidance literature:

With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In 1,2-dimethoxyethane; at 90 ℃; for 1h; Inert atmosphere;

upstream raw materials:

4-iodo-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

1,5-dimethyl-1H-pyrazol-3-ylamine

4,6-dichloro-1-methyl-1H-imidazo [4,5-c]pyridine

(Z)-N,N-dicyclopropyl-6-ethyl-1-methyl-4-(1-(methylthio)-3-oxobut-1-enylamino)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide

Refernces

• 1、 Fitzgerald, Monica A,Soltani, Omid,Wei, Carolyn,Skliar, Dimitri,Zheng, Bin,Li, Jun,Albrecht, Jacob,Schmidt, Michael,Mahoney, Michelle,Fox, Richard J.,Tran, Kristy,Zhu, Keming,Eastgate, Martin D.. "Ni-Catalyzed C-H Functionalization in the Formation of a Complex Heterocycle: Synthesis of the Potent JAK2 Inhibitor BMS-911543". . p. 6001 - 6011. Retrieved 2015.
• 2、 -. "PROCESS FOR THE PREPARATION OF N,N-DICYCLOPROPYL-4-(1,5-DIMETHYL-1H-PYRAZOL-3-YLAMINO)-6-ETHYL-1-METHYL-1,6-DIHYDROIMIDAZO[4,5-d]PYRROLO[2,3-b]PYRIDINE-7-CARBOXAMIDE". . . Retrieved 2015/03/16.