ChemicalBook CAS DataBase List Pomalidomide

Pomalidomide synthesis

5synthesis methods

Product Name:Pomalidomide
CAS Number:19171-19-8
Molecular formula:C13H11N3O4
Molecular Weight:273.24

Pomalidomide, also known as CC4047, is an orally bioavailable derivative of thalidomide with potential immunomodulating, antiangiogenic and antineoplastic activities. Although its exact mechanism of action has yet to be fully elucidated, pomalidomide appears to inhibit TNF-alpha production, enhance the activity of T cells and natural killer (NK) cells and enhance antibody-dependent cellular cytotoxicity (ADCC). Pomalidomide was approved on February 8, 2013 as a treatment for relapsed and refractory multiple myeloma.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

Huang, Daowei; Shen, Chengwu; Wang, Wenya; Huang, Lei; Ni, Feng; Li, Jianqi. New synthesis route for the preparation of pomalidomide. Synthetic Communications. Volume 46. Issue 16. Pages 1343-1348. Journal; Online Computer File. (2016).

2H-Isoindole-2-carboxylic acid, 4-amino-1,3-dihydro-1,3-dioxo-, ethyl ester

340020-02-2
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2353-44-8
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19171-19-8
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Yield:19171-19-8 96.6%

Reaction Conditions:

with sodium acetate in acetonitrile; for 4 h;Reflux;

Steps:

2 Example 2 The production (R/S)-4-amino-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione (1)

40.0 g (170.8 mmol) of ethyl 4-amino-1,3-dioxo-1,3-dihydro-2H-isomdole-2-carboxylate, 800 cm³ of acetonitrile, 28.4 g (342.0 mmol) of anhydrous sodium acetate, 28.1 g (170.7 mmol) of 3-aminopiperidine-2,6-dione are measured into a 1000 cm³ round-bottomed flask, then the suspension obtained in this way is heated to reflux temperature. The stirring is continued at unchanged temperature for 4 hours. The reaction mixture is concentrated to about 40 cm³ at 40 °C with the help of a vacuum. 800 cm³ of distilled water is added to the concentrated residue, which is then stirred at room temperature for 30 minutes. (The water may also be added at an earlier stage.) Following this the crystalline product is filtered, washed with 2x400 cm³ of distilled water, then dried at 50 °C in a vacuum until constant weight is achieved. In this way 45.10 g (96.6%) of the product according to the title is obtained. Mp. : 314-315 °C (decomposes) IR (KBr): 3481 , 3378, 3248, 1752, 1703, 1635, 1362, 1197 cm ¹. 1H NMR (DMSO-d6, 400 MHz): δ = 11.10 (b, 1H), 7.47 (m, 1H), 7.02 (m, 1H), 7.00 (m, 1H), 5.06 (m, 1H), 2.89 (m, 1H), 2.58 (m, 1H), 2.56 (m, 1H), 2.03 (m, 1H) ppm. HPLC: Waters Acquity UPLC BEH C18; 2.1 x50 mm; 1.7 μm; 0.5 mL/min; 225 nm; 10/90 CH₃CN/0.1 % HClO₄ (aq); 1.38 min (99.90%).

References:

WO2017/134476,2017,A1 Location in patent:Page/Page column 16

2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione

19171-18-7
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19171-19-8
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References

444289-17-2
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19171-19-8
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References

24666-56-6 Synthesis

24666-56-6
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6946-22-1
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19171-19-8
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References

24666-56-6 Synthesis

24666-56-6
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19171-19-8
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References

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