2-(4-ethylpiperazin-1-yl)-N-[4-(2-morpholin-4-yl-4-oxochromen-8-yl)dibenzothiophen-1-yl]acetamide

Base Information

• Chemical Name: 2-(4-ethylpiperazin-1-yl)-N-[4-(2-morpholin-4-yl-4-oxochromen-8-yl)dibenzothiophen-1-yl]acetamide
• CAS No.: 881375-00-4
• Molecular Formula: C₃₃H₃₄N₄O₄S
• Molecular Weight: 582.723
• UNII: LM6DZS6PYA
• Nikkaji Number: J3.351.611H
• Wikidata: Q59771381
• Pharos Ligand ID: Y7CKQ2CCX6DZ
• ChEMBL ID: CHEMBL1086377
• Mol file: 881375-00-4.mol

Synonyms:2-(4-ethylpiperazin-1-yl)-N-(4-(2-morpholino-4-oxo-4H-chromen-8-yl)dibenzo(b,d)thiophen-1-yl)acetamide;KU-0060648

Chemical Property of 2-(4-ethylpiperazin-1-yl)-N-[4-(2-morpholin-4-yl-4-oxochromen-8-yl)dibenzothiophen-1-yl]acetamide

Chemical Property:

• Boiling Point: 819.9±65.0 °C(Predicted)
• PKA: 14.10±0.43(Predicted)
• PSA: 106.50000
• Density: 1.337±0.06 g/cm3(Predicted)
• LogP: 5.25430
• Solubility.: Limited solubility, soluble in HCl
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 582.23007675
• Heavy Atom Count: 42
• Complexity: 1010

Purity/Quality:

98% min ^*data from raw suppliers

KU-0060648 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1CCN(CC1)CC(=O)NC2=C3C4=CC=CC=C4SC3=C(C=C2)C5=CC=CC6=C5OC(=CC6=O)N7CCOCC7
• Uses: KU-0060648 is a dual inhibitor of DNA-PK and PI3Kα, PI3Kβ, PI3Kδ.

Technology Process of 2-(4-ethylpiperazin-1-yl)-N-[4-(2-morpholin-4-yl-4-oxochromen-8-yl)dibenzothiophen-1-yl]acetamide

There total 11 articles about 2-(4-ethylpiperazin-1-yl)-N-[4-(2-morpholin-4-yl-4-oxochromen-8-yl)dibenzothiophen-1-yl]acetamide 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:

2-morpholino-8-(1-nitrodibenzo[b,d]thiophen-4-yl)-4H-chromen-4-one (881375-80-0) → KU-0060648 (881375-00-4)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; zinc / 25 °C

2: triethylamine / N,N-dimethyl acetamide / 18 h / 25 °C

3: N,N-dimethyl acetamide / 18 h / 25 °C

With acetic acid; triethylamine; zinc; In N,N-dimethyl acetamide;

DOI:10.1021/jm400915j

Reference yield:

8-(1-aminodibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (881375-81-1) → KU-0060648 (881375-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / N,N-dimethyl acetamide / 18 h / 25 °C

2: N,N-dimethyl acetamide / 18 h / 25 °C

With triethylamine; In N,N-dimethyl acetamide;

DOI:10.1021/jm400915j

Reference yield:

dibenzothiophene (132-65-0) → KU-0060648 (881375-00-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: n-butyllithium / tetrahydrofuran / Reflux

1.2: 25 °C

2.1: potassium carbonate / acetone / Reflux

3.1: nitric acid; acetic acid / 25 °C

4.1: pyridine hydrochloride / 150 °C

5.1: triethylamine / dichloromethane / 0 °C

6.1: 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 95 °C / Inert atmosphere

7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / tetrahydrofuran / 18 h / 80 - 85 °C / Schlenk technique; Inert atmosphere

8.1: acetic acid; zinc / 25 °C

9.1: triethylamine / N,N-dimethyl acetamide / 18 h / 25 °C

10.1: N,N-dimethyl acetamide / 18 h / 25 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; n-butyllithium; nitric acid; potassium acetate; pyridine hydrochloride; potassium carbonate; caesium carbonate; acetic acid; triethylamine; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl acetamide; acetone; 7.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/jm400915j

upstream raw materials:

2-morpholino-8-(1-nitrodibenzo[b,d]thiophen-4-yl)-4H-chromen-4-one

8-(1-aminodibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one

4-ethylpiperazine

2-chloro-N-[4-(2-morpholin-4-yl-4-oxo-4H-chromen-8-yl)-dibenzothiophen-1-yl]-acetamide

Refernces

• 1、 -. "DNA-PK INHIBITORS". Page/Page column 42; 45. . Retrieved 2008/06/13.