Insulin-like Growth Factor-1 Receptor Inhibitor

Base Information

• Chemical Name: Insulin-like Growth Factor-1 Receptor Inhibitor
• CAS No.: 468740-43-4
• Molecular Formula: C25H26ClN5O3
• Molecular Weight: 479.966
• Mol file: 468740-43-4.mol

Synonyms:4-{[(2S)-2-(3-Chlorophenyl)-2-hydroxyethyl]amino}-3-(4-methyl-6-morpholin-4-yl-1H-benzimidazol-2-yl)pyridin-2(1H)-one;

Chemical Property of Insulin-like Growth Factor-1 Receptor Inhibitor

Chemical Property:

• Refractive Index: 1.717
• PKA: 10.40±0.10(Predicted)
• PSA: 106.27000
• Density: 1.44 g/cm³
• LogP: 4.00010
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

BMS 536924 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: BMS 536924 is an inhibitor of insulin-like growth factor receptor (IGF1R) kinase and insulin receptor. BMS 536924 was reported to have antitumor activity.

Technology Process of Insulin-like Growth Factor-1 Receptor Inhibitor

There total 7 articles about Insulin-like Growth Factor-1 Receptor Inhibitor 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: 75.0%

(S)-2-amino-1-(3-chlorophenyl)ethanol hydrochloride (169032-01-3) + 4-chloro-3-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-one + 4-iodo-3-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-one → (S)-4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-one (468740-43-4)

Guidance literature:

(S)-2-amino-1-(3-chlorophenyl)ethanol hydrochloride; 4-chloro-3-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-one; 4-iodo-3-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-one; With triethylamine; In acetonitrile; at 85 ℃;

With caesium carbonate; In water; Sonographic reaction;

Reference yield:

2-methyl-4-(morpholin-4-yl)-6-nitroaniline (468741-20-0) → (S)-4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-one (468740-43-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂ / Pd/C / methanol / 3102.89 Torr

2.1: 15.58 g / air / methanol / 48 h / 0 - 20 °C

3.1: HCl / dioxane; H₂O / 20 - 50 °C

3.2: 3.951 g / Et₃N / acetonitrile / 85 °C

With hydrogenchloride; air; hydrogen; palladium on activated charcoal; In 1,4-dioxane; methanol; water;

DOI:10.1021/jm050392q

Reference yield:

4-bromo-2-methyl-6-nitroaniline (77811-44-0) → (S)-4-[2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-3-(4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-1H-pyridin-2-one (468740-43-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 61 percent / tris(dibenzylideneacetone)dipalladium; 2-(di-tert-butylphosphanyl)biphenyl; t-BuONa / tetrahydrofuran / 18 h / 85 °C

2.1: H₂ / Pd/C / methanol / 3102.89 Torr

3.1: 15.58 g / air / methanol / 48 h / 0 - 20 °C

4.1: HCl / dioxane; H₂O / 20 - 50 °C

4.2: 3.951 g / Et₃N / acetonitrile / 85 °C

With hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; air; hydrogen; johnphos; sodium t-butanolate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1021/jm050392q

upstream raw materials:

(S)-2-amino-1-(3-chlorophenyl)ethanol hydrochloride

2-(4-iodo-2-methoxypyridin-3-yl)-4-methyl-6-(morpholin-4-yl)-1H-benzimidazole

2-methyl-4-(morpholin-4-yl)-6-nitroaniline

3-chlorophenacyl chloride