5-[[4-(4-Pyridinyl)-6-quinolinyl]methylene]-2,4-thiazolidenedione

Base Information

• Chemical Name: 5-[[4-(4-Pyridinyl)-6-quinolinyl]methylene]-2,4-thiazolidenedione
• CAS No.: 958852-01-2
• Molecular Formula: C₁₈H₁₁N₃O₂S
• Molecular Weight: 333.37
• Mol file: 958852-01-2.mol

Synonyms:5-[[4-(4-Pyridinyl)-6-quinolinyl]methylene]-2,4-thiazolidenedione;GSK 1059615;(5Z)-5-[[4-(4-Pyridinyl)-6-quinolinyl]methylene]-2,4-thiazolidinedione;GSK 1059615 SodiuM Salt Hydrate

Chemical Property of 5-[[4-(4-Pyridinyl)-6-quinolinyl]methylene]-2,4-thiazolidenedione

Chemical Property:

• PSA: 97.25000
• LogP: 3.94950
• Storage Temp.: Store at +4°C
• Solubility.: H2O: ≥8mg/mL

Purity/Quality:

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

GSK 1059615 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: GSK 1059615 is a potent inhibitor of PI 3-kinase α (PI3Kα). GSK 1059615 inhibits proliferation in BT474 cells and attenuates MAPK signaling. GSK 1059615 is a potent inhibitor of PI 3-kinase and FRAP (mTOR).

Technology Process of 5-[[4-(4-Pyridinyl)-6-quinolinyl]methylene]-2,4-thiazolidenedione

There total 4 articles about 5-[[4-(4-Pyridinyl)-6-quinolinyl]methylene]-2,4-thiazolidenedione 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: 50.0%

thiazoline-2,4-dione (2295-31-0) + 4-(4-pyridinyl)-6-quinolinecarbaldehyde (958852-13-6) → GSK1059615 (958852-01-2)

Guidance literature:

With piperidine; acetic acid; In ethanol; at 150 ℃; for 0.5h; Irradiation;

Reference yield:

6-bromo-4-chloroquinoline (65340-70-7) → GSK1059615 (958852-01-2)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 2 h / Heating / reflux

2: 2,6-dimethylpyridine; sodium periodate; water / osmium(VIII) oxide / 1,4-dioxane; tert-butyl alcohol / 3.5 h / 20 °C

3: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 3 h / 100 °C

4: piperidine; acetic acid / ethanol / 0.5 h / 150 °C / Irradiation

With piperidine; 2,6-dimethylpyridine; sodium periodate; water; potassium carbonate; acetic acid; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Suzuki Coupling;

Reference yield:

4-chloro-6-vinylquinoline (916811-99-9) → GSK1059615 (958852-01-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-dimethylpyridine; sodium periodate; water / osmium(VIII) oxide / 1,4-dioxane; tert-butyl alcohol / 3.5 h / 20 °C

2: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 3 h / 100 °C

3: piperidine; acetic acid / ethanol / 0.5 h / 150 °C / Irradiation

With piperidine; 2,6-dimethylpyridine; sodium periodate; water; potassium carbonate; acetic acid; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Suzuki Coupling;

upstream raw materials:

thiazoline-2,4-dione

4-(4-pyridinyl)-6-quinolinecarbaldehyde

4-chloroquinoline-6-carbaldehyde

4-pyridylboronic acid

Refernces