S-Pomalidomide

Base Information

• Chemical Name: S-Pomalidomide
• CAS No.: 202271-89-4
• Molecular Formula: C13H11N3O4
• Molecular Weight: 273.24400
• UNII: 2EE4M42K6G
• Nikkaji Number: J1.121.696J
• Wikidata: Q27254625
• ChEMBL ID: CHEMBL2093113
• Mol file: 202271-89-4.mol

Synonyms:(S)-pomalidomide;202271-89-4;Pomalidomide, (S)-;S-Pomalidomide;Pomalidomide, (-)-;2EE4M42K6G;(S)-CC-4047;4-AMINO-2-[(3S)-2,6-DIOXOPIPERIDIN-3-YL]ISOINDOLE-1,3-DIONE;(S)-4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione;(s)-4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione;1H-Isoindole-1,3(2H)-dione, 4-amino-2-((3S)-2,6-dioxo-3-piperidinyl)-;1H-Isoindole-1,3(2H)-dione, 4-amino-2-(2,6-dioxo-3-piperidinyl)-, (S)-;1H-Isoindole-1,3(2H)-dione, 4-amino-2-((3S)-2,6-dioxo-3-piperidinyl)-, (-)-;Y70;4ci3;UNII-2EE4M42K6G;SCHEMBL563317;CHEMBL2093113;PD132344;Q27254625;2-[(3S)-2,6-Dioxo-3-piperidinyl]-4-aminoisoindoline-1,3-dione

Chemical Property of S-Pomalidomide

Chemical Property:

• PSA: 109.57000
• LogP: 0.51790
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 273.07495584
• Heavy Atom Count: 20
• Complexity: 504

Purity/Quality:

99% ^*data from raw suppliers

(S)-Pomalidomide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)N
• Isomeric SMILES: C1CC(=O)NC(=O)[C@H]1N2C(=O)C3=C(C2=O)C(=CC=C3)N
• Uses: (S)-Pomalidomide is a stereoisomer of Pomalidomide (P688205), a potent inhibitor of TNF-α production. It is an antiinflammatory and antitumor agent used in the treatment of multiple myeloma.

Technology Process of S-Pomalidomide

There total 58 articles about S-Pomalidomide 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: 96.6%

ethyl 4-amino-1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate (340020-02-2) + (+/-)-α-aminoglutarimide (2353-44-8,673485-72-8) → pomalidomide (19171-19-8,202271-89-4)

Guidance literature:

With sodium acetate; In acetonitrile; for 4h; Reflux;

Reference yield: 96.0%

C14H15N3O5 → pomalidomide (19171-19-8,202271-89-4)

Guidance literature:

In acetonitrile; at 80 ℃; for 2.5h; Solvent; Temperature;

Reference yield: 95.6%

N-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)acetamide (444289-17-2) → pomalidomide (19171-19-8,202271-89-4)

Guidance literature:

With sodium hydroxide; In water; acetonitrile; at 80 ℃; for 8h; Reagent/catalyst; Temperature; Solvent;

upstream raw materials:

(R)-2-(2,6-dioxo(3-piperidyl))-4-nitroisoindoline-1,3-dione

4-nitro-1H-isoindole-1,3(2H)-dione

ethyl 4-nitro-1,3-dioxoisoindoline-2-carboxylate

N-(3-nitrophthaloyl)-D-glutamine

Refernces

• 1、 Konstantinidou, Markella,Oun, Asmaa,Pathak, Pragya,Zhang, Bidong,Wang, Zefeng,ter Brake, Frans,Dolga, Amalia M.,Kortholt, Arjan,D?mling, Alexander. "The tale of proteolysis targeting chimeras (PROTACs) for Leucine-Rich Repeat Kinase 2 (LRRK2)". supporting information. p. 959 - 965. Retrieved 2020/12/30.
• 2、 Kim, Ga Yeong,Song, Chae Won,Yang, Yo-Sep,Lee, Na-Rae,Yoo, Hyung-Seok,Son, Seung Hwan,Lee, Soo Jin,Park, Jong Seon,Lee, Jong Kil,Inn, Kyung-Soo,Kim, Nam-Jung. "Chemical degradation of androgen receptor (Ar) using bicalutamide analog–thalidomide protacs". . . Retrieved 2021/05/26.