GSK-3326595

Base Information

• Chemical Name: GSK-3326595
• CAS No.: 1616392-22-3
• Molecular Formula: C₂₄H₃₂N₆O₃
• Molecular Weight: 452.556
• Mol file: 1616392-22-3.mol

Synonyms:

Chemical Property of GSK-3326595

Chemical Property:

• Boiling Point: 760.3±60.0 °C(Predicted)
• PKA: 12.44±0.46(Predicted)
• Density: 1.275±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Soluble in DMSO (up to 20 mg/ml).

Purity/Quality:

99%, ^*data from raw suppliers

EPZ015938(pemrametostat) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: GSK3326595 (1616395-22-3) is a potent (IC50?= 6.2nM), selective (>4000-fold over 20 other methyltransferases), SAM uncompetitive, peptide competitive inhibitor of PRMT5.1?PRMT5 inhibition activated the p53 pathway?via?induction of alternative splicing of MDM4 leading to a potent anti-proliferative response both?in vitro?and?in vivo. Combination therapy with palbociclib (CDK4/6 inhibitor, Focus Cat.# 10-4760) and GSK3326595 lead to increased efficacy of palbociclib in treating native and resistant models of melanoma via regulation of the PRMT5-MDM4 axis.2?Currently in clinical trials.3
• Uses: GSK-3326595 is a protein arginine methyltransferase 5(PRMT5) inhibitor under clinical trial.

Technology Process of GSK-3326595

There total 6 articles about GSK-3326595 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:

(S)-6-chloro-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)pyrimidine-4-carboxamide + 1-(4-amino-piperidin-1-yl)-ethanone (160357-94-8) → GSK-3326595 (1616392-22-3)

Guidance literature:

With triethylamine; In isopropyl alcohol; at 60 ℃; for 16h;

Reference yield:

1,2,3,4-tetrahydroisoquinoline (91-21-4) → GSK-3326595 (1616392-22-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium fluoride / tetrahydrofuran / 1 h / 0 °C

1.2: 16 h / 22 °C

2.1: ammonia / ethanol / 3 h / -78 - 80 °C / Sealed tube

3.1: triethylamine / dichloromethane / 2 h / -60 - 10 °C

4.1: triethylamine / isopropyl alcohol / 16 h / 60 °C

With potassium fluoride; ammonia; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; isopropyl alcohol;

Reference yield:

6-hydroxypyrimidine-4-carboxylic acid (6299-87-2) → GSK-3326595 (1616392-22-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride / ethyl acetate / 0.5 h / 20 - 30 °C

1.2: 16 h / 80 °C

2.1: triethylamine / dichloromethane / 2 h / -60 - 10 °C

3.1: triethylamine / isopropyl alcohol / 16 h / 60 °C

With oxalyl dichloride; triethylamine; In dichloromethane; ethyl acetate; isopropyl alcohol;

upstream raw materials:

1,2,3,4-tetrahydroisoquinoline

1-(4-amino-piperidin-1-yl)-ethanone

6-hydroxypyrimidine-4-carboxylic acid

6-chloropyrimidine-4-carbonyl chloride

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