KX2-391

Base Information

• Chemical Name: KX2-391
• CAS No.: 897016-82-9
• Molecular Formula: C26H29N3O3
• Molecular Weight: 431.535
• Mol file: 897016-82-9.mol

Synonyms:5-[4-[2-(4-Morpholinyl)ethoxy]phenyl]-N-(phenylmethyl)-2-pyridineacetamide; KX 01

Chemical Property of KX2-391

Chemical Property:

• Boiling Point: 680.859 °C at 760 mmHg
• PKA: 14.73±0.46(Predicted)
• Flash Point: 365.57 °C
• PSA: 67.18000
• Density: 1.169 g/cm³
• LogP: 4.09670
• Solubility.: insoluble in H2O; ≥121 mg/mL in DMSO; ≥2.44 mg/mL in EtOH with gentle warming and ultrasonic

Purity/Quality:

98% min ^*data from raw suppliers

KX2-391 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A synthetic, orally bioavailable small molecule and non-ATP competitive Src tyrosine kinase inhibitor with an IC50 of average 72 nM.

Technology Process of KX2-391

There total 10 articles about KX2-391 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: 90.0%

methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate (1038395-64-0) + benzylamine (100-46-9) → KX2-391 (897016-82-9)

Guidance literature:

In methoxybenzene; at 142 ℃; for 48h; Product distribution / selectivity;

Reference yield: 79.0%

N-benzyl-2-(5-bromopyridin-2-yl)acetamide + 4-(2-( 4-( 4, 4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)morpholine (690636-28-3) → KX2-391 (897016-82-9)

Guidance literature:

With potassium carbonate; FibreCat 1007; In ethanol; water; at 150 ℃; for 0.166667h; Microwave irradiation;

Reference yield:

1-bromo-4-(2-morpholinoethoxy)benzene (836-59-9) → KX2-391 (897016-82-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,2-dimethoxyethane; water

2: sodium hexamethyldisilazane / Cooling with ice

3: sulfuric acid

4: methoxybenzene / Heating

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; sodium hexamethyldisilazane; sodium carbonate; methoxybenzene; In 1,2-dimethoxyethane; water; 1: |Suzuki Coupling;

upstream raw materials:

4-(2-( 4-( 4, 4, 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)morpholine

methyl 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)acetate

benzylamine

4-bromo-phenol

Downstream raw materials:

2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide dihydrochloride

2-(5-(4-(2-morpholin-4-ylethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide hydrochloride

2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide mesylate

Refernces

• 1、 Smolinski, Michael P.,Bu, Yahao,Clements, James,Gelman, Irwin H.,Hegab, Taher,Cutler, David L.,Fang, Jane W. S.,Fetterly, Gerald,Kwan, Rudolf,Barnett, Allen,Lau, Johnson Y. N.,Hangauer, David G.. "Discovery of Novel Dual Mechanism of Action Src Signaling and Tubulin Polymerization Inhibitors (KX2-391 and KX2-361)". supporting information. p. 4704 - 4719. Retrieved 2018/06/20.
• 2、 -. "PHARMACEUTICAL COMPOSITIONS FOR MODULATING A KINASE CASCADE AND METHODS OF USE THEREOF". Page/Page column 52-53. . Retrieved 2009/05/28.