GSK2110183B

Base Information

• Chemical Name: GSK2110183B
• CAS No.: 1047645-82-8
• Molecular Formula: C18H18Cl3FN4OS
• Molecular Weight: 463.791
• Mol file: 1047645-82-8.mol

Synonyms:Afuresertib (hydrochloride);GSK 2110183B;GSK2110183B;GSK-2110183B;GSK 2110183 hydrochloride;GSK2110183 hydrochloride;GSK-2110183 hydrochloride;N-((S)-1-Amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide hydrochloride

Chemical Property of GSK2110183B

Chemical Property:

• PSA: 101.18000
• LogP: 5.78750

Purity/Quality:

99%+, ^*data from raw suppliers

AfuresertibHCl >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Afuresertib is a selective, orally bioavailable inhibitor of Akt1, 2, and 3 with Ki values of 0.08, 2, and 2.6 nM, respectively. It preferentially inhibits the proliferation of human cancer cell lines with Akt pathway activation and various cell lines derived from hematologic malignancies with minimal effect on glucose homeostasis. Afuresertib demonstrates activity against multiple myeloma in both preclinical and clinical models.[Cayman Chemical]

Technology Process of GSK2110183B

There total 6 articles about GSK2110183B 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: 73.6%

N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl] ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide (1047644-62-1) → N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride (1047645-82-8)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; tert-butyl methyl ether; acetonitrile; at 40 - 42 ℃; Product distribution / selectivity;

Reference yield:

5-Chlorothiophene-2-carboxylic acid (24065-33-6) → N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride (1047645-82-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid / 12 - 20 h / 50 - 55 °C

2.1: aluminum (III) chloride; bromine / chloroform / 6 h / 25 °C

3.1: potassium carbonate / bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane; water / 1.5 h / 75 °C

4.1: N-chloro-succinimide / tetrahydrofuran / 4 h / 70 °C

4.2: 2 h

5.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 12 h / 20 °C

6.1: hydrazine / tetrahydrofuran; methanol / 24 h / 20 °C

7.1: hydrogenchloride / 1,4-dioxane / 0.08 h

With hydrogenchloride; aluminum (III) chloride; N-chloro-succinimide; sulfuric acid; bromine; potassium carbonate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; hydrazine; bis(tri-t-butylphosphine)palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water;

Reference yield:

methyl 4-bromo-5-chlorothiophene-2-carboxylate (1047630-72-7) → N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride (1047645-82-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / bis(tri-t-butylphosphine)palladium⁽⁰⁾ / 1,4-dioxane; water / 1.5 h / 75 °C

2.1: N-chloro-succinimide / tetrahydrofuran / 4 h / 70 °C

2.2: 2 h

3.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane / 12 h / 20 °C

4.1: hydrazine / tetrahydrofuran; methanol / 24 h / 20 °C

5.1: hydrogenchloride / 1,4-dioxane / 0.08 h

With hydrogenchloride; N-chloro-succinimide; potassium carbonate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; hydrazine; bis(tri-t-butylphosphine)palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

upstream raw materials:

N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl] ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

5-Chlorothiophene-2-carboxylic acid

methyl 4-bromo-5-chlorothiophene-2-carboxylate

methyl 5-chloro-4-iodo-2-thiophenecarboxylate

Refernces

• 1、 -. "INHIBITORS OF AKT ACTIVITY". Page/Page column 191-192. . Retrieved 2008/12/08.