GW441756

Base Information

• Chemical Name: GW441756
• CAS No.: 504433-23-2
• Molecular Formula: C₁₇H₁₃N₃O
• Molecular Weight: 275.31
• Mol file: 504433-23-2.mol

Synonyms:1,3-Dihydro-3-[(1-methyl-1H-indol-3-yl)methylene]-2H-pyrrolo[3,2-b]pyr

Chemical Property of GW441756

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.708
• Boiling Point: 567.985 °C at 760 mmHg
• PKA: 11.04±0.20(Predicted)
• Flash Point: 297.307 °C
• PSA: 46.92000
• Density: 1.318 g/cm³
• LogP: 3.20400
• Storage Temp.: Store at RT
• Solubility.: Soluble in DMSO (up to 5 mg/ml).

Purity/Quality:

98%,99%, ^*data from raw suppliers

GW441756 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: GW-441756 (504433-23-2) is a potent and selective TrkA kinase inhibitor (IC50 = 2 nM).
• Uses: GW 441756 is an effective Trk binder, a novel bioactive molecule used in the treatment of neuroblastoma in infants.

Technology Process of GW441756

There total 7 articles about GW441756 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:

N-methyl-3-formylindole (19012-03-4) + diethyl 2-(2-bromopyridin-3-ylamino)-2-oxoethylphosphonate (1243657-75-1) → (E)-3-((1-methyl-1H-indol-3-yl)methylene)-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (1243657-78-4,504433-23-2) + GW441756 (504433-24-3,504433-23-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,2-dimethoxyethane; at 130 ℃; for 1h; optical yield given as %de; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.tet.2010.03.018

Reference yield:

N-methyl-3-formylindole (19012-03-4) + diethyl 2-(2-bromopyridin-3-ylamino)-2-oxoethylphosphonate (1243657-75-1) → (E)-3-((1-methyl-1H-indol-3-yl)methylene)-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (1243657-78-4,504433-23-2) + GW441756 (504433-24-3,504433-23-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,2-dimethoxyethane; at 130 ℃; for 1h; optical yield given as %de; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.tet.2010.03.018

Reference yield:

2-Chloro-3-nitropyridine (5470-18-8,34515-82-7) → GW441756 (504433-23-2)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethylsulfoxide

2: aq. LiCl / dimethylsulfoxide

3: H₂ / Pd/C / ethanol / 2068.59 Torr

4: HCl / diethyl ether

5: HCl; AcOH / 50 - 100 °C

With hydrogenchloride; hydrogen; acetic acid; lithium chloride; palladium on activated charcoal; In diethyl ether; ethanol; dimethyl sulfoxide;

DOI:10.1016/j.bmcl.2003.12.002

upstream raw materials:

N-methyl-3-formylindole

1,3-dihydro-2H-pyrrolo[3,2-b]pyridin-2-one

2-Chloro-3-nitropyridine

diethyl 2-(3-nitropyridin-2-yl)malonate

Refernces

• 1、 Wood, Edgar R.,Kuyper, Lee,Petrov, Kimberly G.,Hunter III, Robert N.,Harris, Philip A.,Lackey, Karen. "Discovery and in vitro evaluation of potent TrkA kinase inhibitors: Oxindole and aza-oxindoles". . p. 953 - 957. Retrieved 2007/10/03.