GSK-2110183C

Base Information

• Chemical Name: GSK-2110183C
• CAS No.: 1047644-62-1
• Molecular Formula: C18H17Cl2FN4OS
• Molecular Weight: 427.33
• Mol file: 1047644-62-1.mol

Synonyms:Afuresertib;GSK 2110183C;GSK2110183C;GSK-2110183C;N-((S)-1-amino-3-(3-fluorophenyl)propan-2-yl)-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxamide;Afuresertib(GSK2110183C);Afuresertib, GSK-2110183, GSK-2110183B;Delitinib

Chemical Property of GSK-2110183C

Chemical Property:

• Boiling Point: 535.1±50.0 °C(Predicted)
• PKA: 13.03±0.46(Predicted)
• PSA: 101.18000
• Density: 1.49±0.1 g/cm3(Predicted)
• LogP: 4.98550

Purity/Quality:

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

Afuresertib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Afuresertib is a potent pan-AKT inhibitor that demonstrated synergy with bortezomib in preclinical models of multiple myeloma.

Technology Process of GSK-2110183C

There total 15 articles about GSK-2110183C 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%

methyl (2S)-2-{[5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)thiophen-2-yl]formamido}-3-(3-fluorophenyl)propanoate → 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)

Guidance literature:

methyl (2S)-2-{[5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)thiophen-2-yl]formamido}-3-(3-fluorophenyl)propanoate; With ammonia; In methanol; at 25 - 30 ℃; for 18h; Inert atmosphere;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 70 - 75 ℃; for 48h; Reagent/catalyst; Inert atmosphere;

Reference yield:

5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-{(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}-2-thiophenecarboxamide (1047645-80-6) → 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)

Guidance literature:

With hydrazine; In tetrahydrofuran; methanol;

DOI:10.1358/dof.2014.039.08.2177902

Reference yield:

methyl 5-chloro-2-thiophenecarboxylate (35475-03-7) → 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)

Guidance literature:

Multi-step reaction with 6 steps

1: N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride / acetic acid / 70 °C

2: C₂₄H₅₄P₂Pd; potassium carbonate / 1,4-dioxane; water / 70 °C

3: N-chloro-succinimide / tetrahydrofuran / 70 °C

4: sodium hydroxide / tetrahydrofuran; water; methanol

5: N-ethyl-N,N-diisopropylamine; PyBroP / dichloromethane

6: hydrazine / tetrahydrofuran; methanol

With N-chloro-succinimide; C₂₄H₅₄P₂Pd; potassium carbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate; N-ethyl-N,N-diisopropylamine; PyBroP; sodium hydroxide; zinc(II) chloride; hydrazine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetic acid;

DOI:10.1358/dof.2014.039.08.2177902

upstream raw materials:

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

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

methyl 5-chloro-4-(1-methylpyrazol-5-yl)-2-thiophenecarboxylate

5-Chlorothiophene-2-carboxylic acid

Downstream raw materials:

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

Refernces

• 1、 -. "Preparation method of Afuresertib". . . Retrieved 2020/09/16.
• 2、 -. "INHIBITORS OF AKT ACTIVITY". Page/Page column 191-192. . Retrieved 2008/12/08.