GNE-3511

Base Information

• Chemical Name: GNE-3511
• CAS No.: 1496581-76-0
• Molecular Formula: C₂₃H₂₆F₂N₆O
• Molecular Weight: 440.496
• Hs Code.: 2934999090
• Mol file: 1496581-76-0.mol

Synonyms:

Chemical Property of GNE-3511

Chemical Property:

• Boiling Point: 579.0±50.0 °C(Predicted)
• PKA: 7.23±0.40(Predicted)
• Density: 1.37±0.1 g/cm3(Predicted)

Purity/Quality:

99%, ^*data from raw suppliers

GNE-3511 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: GNE-3511 is a selective and highly potent inhibitor of dual leucine zipper kinase (DLK). It also inhibits phosphorylated JNKand is highly selective for DLK over other MAP kinases. In an MPTP mouse model of Parkinson’s disease, a high dose of GNE-3511 completely suppresses phosphorylated c-Jun (p-c-Jun) expression, while a low dose moderately reduces its expression. Study has also shown that GNE03511 displayed concentration-dependent protection of neurons from degeneration in vitro and demonstrated dose-dependent activity in two different animal models of disease. These results suggest that GNE-3511 may have therapeutic potential in multiple indications.
• Uses: GNE-3511 is a potent and selective dual leucine zipper kinase (DLK, MAP3K12) inhibitors with activity in neurodegeneration models. GNE-3511 displays concentration-dependent protection of neurons from degeneration in vitro and demonstrated dose-dependent activity in two different animal models of disease. GNE-3511 displays protection of primary neurons in an in vitro axon degeneration assay as well as activity in the mouse models of glaucoma/optic neuropathy (optic nerve crush) and Parkinson’s disease (MPTP) after oral dosing.

Technology Process of GNE-3511

There total 7 articles about GNE-3511 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: 77.0%

2-chloro-6-(3,3-difluoropyrrolidin-1-yl)-4-(1-(oxetan-3-yl)-piperidin-4-yl)pyridine + 4-cyanopyridin-2-amine (42182-27-4) → 2-((6-(3,3-difluoropyrrolidin-1-yl)-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-2-yl)amino)isonicotinonitrile (1496581-76-0)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; for 13h; Reflux; Inert atmosphere;

Reference yield:

2,6-dichloro-4-iodopyridine (98027-84-0) → 2-((6-(3,3-difluoropyrrolidin-1-yl)-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-2-yl)amino)isonicotinonitrile (1496581-76-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 0.67 h / Inert atmosphere

1.2: 16.5 h / 80 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 1.5 h / 130 °C / Microwave irradiation

3.1: trifluoroacetic acid / dichloromethane / 2 h / Cooling with ice

3.2: 0.58 h / 24 °C

4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 13 h / Reflux; Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; chloro-trimethyl-silane; caesium carbonate; ethylene dibromide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; dichloromethane; N,N-dimethyl acetamide;

Reference yield:

tert-butyl 4-(2-chloro-6-(3 ,3-difluoropyrrolidin-1-yl)pyridin-4-yl)piperidine-1-carboxylate → 2-((6-(3,3-difluoropyrrolidin-1-yl)-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-2-yl)amino)isonicotinonitrile (1496581-76-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 2 h / Cooling with ice

1.2: 0.58 h / 24 °C

2.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 13 h / Reflux; Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; trifluoroacetic acid; In 1,4-dioxane; dichloromethane;

upstream raw materials:

2,6-dichloro-4-iodopyridine

4-cyanopyridin-2-amine

tert-butyl 4-iodopiperidine-1-carboxylate

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