N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)acetamide

Base Information

• Chemical Name: N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)acetamide
• CAS No.: 1421593-80-7
• Molecular Formula: C₁₅H₁₅N₃O₄
• Molecular Weight: 301.302
• Mol file: 1421593-80-7.mol

Synonyms:

Chemical Property of N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)acetamide

Chemical Property:

• Melting Point: >264°C (dec.)
• Boiling Point: 679.7±55.0 °C(Predicted)
• Density: 1.446±0.06 g/cm3(Predicted)

Purity/Quality:

>95% ^*data from raw suppliers

N-[2-(2,6-Dioxo-3-piperidinyl)-2,3-dihydro-1-oxo-1H-isoindol-4-yl]-acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-[2-(2,6-Dioxo-3-piperidinyl)-2,3-dihydro-1-oxo-1H-isoindol-4-yl]-acetamide is a related compound of Lenalidomide (L328000), an immunomodulatory drug and an analog of Thalidomide.

Technology Process of N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)acetamide

There total 9 articles about N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-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: 71.0%

→ N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)acetamide (1421593-80-7)

Guidance literature:

In tetrahydrofuran; Reflux;

Reference yield: 53.0%

acetyl chloride (75-36-5) + Lenalidomide (879126-98-4,879126-99-5,191732-72-6) → N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)acetamide (1421593-80-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1016/j.bmcl.2017.07.046

Reference yield:

Boc-Gln-OH (13726-85-7) → N-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)acetamide (1421593-80-7)

Guidance literature:

Multi-step reaction with 5 steps

1: dicyclohexyl-carbodiimide; dmap / acetonitrile / 20 °C

2: trifluoroacetic acid / dichloromethane / 20 °C

3: potassium hydrogencarbonate / acetonitrile / Reflux

4: hydrogen; palladium on activated charcoal / methanol / 20 °C

5: triethylamine / tetrahydrofuran / 6 h / 20 °C

With dmap; palladium on activated charcoal; hydrogen; potassium hydrogencarbonate; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.bmcl.2017.07.046

upstream raw materials:

acetyl chloride

Lenalidomide

Boc-Gln-OH

(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Refernces

• 1、 -. "TUNABLE ENDOGENOUS PROTEIN DEGRADATION WITH HETEROBIFUNCTIONAL COMPOUNDS". Page/Page column 283; 285. . Retrieved 2018/09/08.