birinapant

Base Information

• Chemical Name: birinapant
• CAS No.: 1260251-31-7
• Molecular Formula: C₄₂H₅₆F₂N₈O₆
• Molecular Weight: 806.953
• Hs Code.: 29339900
• Mol file: 1260251-31-7.mol

Synonyms:

Chemical Property of birinapant

Chemical Property:

• Melting Point: >245oC (dec.)
• Boiling Point: 1090.5±65.0 °C(Predicted)
• PKA: 13.99±0.46(Predicted)
• Density: 1.320±0.06(20.0000℃)
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

Birinapant ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Birinapant is a bivalent mimetic of the Diablo homolog known as second mitochondria-derived activator of caspase (Smac). It is an antagonist of cellular inhibitor of apoptosis 1 (cIAP1, or BIRC2), cIAP2 (BIRC3), and XIAP (BIRC4), binding each at nanomolar concentrations. Birinapant causes rapid cIAP1 degradation, caspase activation, PARP cleavage, and NF-κB activation in breast cancer cells. It shows in vivo antitumor activity, inducing apoptosis in several types of cancer xenografts in mice.
• Uses: Birinapant is a bivalent SMAC mimetic compound antagonist of TRAF2 associated cIAP1 and cIAP2.

Technology Process of birinapant

There total 26 articles about birinapant 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:

acetic acid 3S-{5R-(3'-{4S-acetoxy-1-[2S-(2S-methylaminopropionylamino)butyryl]pyrrolidin-2R-ylmethyl}-6,6'-difluoro-1H,1'H-[2,2']biindol-3-ylmethyl)-1-[2S-(2S-methylaminopropionylamino)butyryl]pyrrolidin}-3-yl ester (1260251-30-6) → birinapant (1260251-31-7)

Guidance literature:

With water; sodium hydroxide; In methanol; at 0 ℃; for 1h; Inert atmosphere;

Reference yield:

(2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(6-fluoro-1H-indole-3-carbonyl)pyrrolidine-1-carboxylic acid benzyl ester (1174655-34-5) → birinapant (1260251-31-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 57 h / 20 °C

2.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 17 h / 2 - 20 °C

3.1: methanol; sodium hydroxide / tetrahydrofuran; water / 2 h

4.1: lithium borohydride / tetrahydrofuran / 2.61 h

4.2: 16 h

5.1: dmap / dichloromethane / 16 h / 20 °C

6.1: trifluoroacetic acid / ethyl acetate / 4.75 h / 2 - 4 °C

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / ethyl acetate / 3 h

8.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; methanol / 3 h / 2585.81 Torr

9.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / 16 h / 0 - 20 °C

10.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C

11.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / 16 h / 0 - 20 °C

12.1: trifluoroacetic acid / dichloromethane / 4.5 h / 0 - 20 °C

13.1: methanol; sodium hydroxide / water / 1 h / 0 °C / Inert atmosphere

With 4-methyl-morpholine; methanol; dmap; lithium borohydride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

(2S,4R)-2-(6-fluoro-1H-indol-3-carbonyl)-4-hydroxypyrrolidine-1-carboxylic acid benzyl ester (1174655-35-6) → birinapant (1260251-31-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 17 h / 2 - 20 °C

2.1: methanol; sodium hydroxide / tetrahydrofuran; water / 2 h

3.1: lithium borohydride / tetrahydrofuran / 2.61 h

3.2: 16 h

4.1: dmap / dichloromethane / 16 h / 20 °C

5.1: trifluoroacetic acid / ethyl acetate / 4.75 h / 2 - 4 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / ethyl acetate / 3 h

7.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; methanol / 3 h / 2585.81 Torr

8.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / 16 h / 0 - 20 °C

9.1: trifluoroacetic acid / dichloromethane / 3 h / 0 °C

10.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / 16 h / 0 - 20 °C

11.1: trifluoroacetic acid / dichloromethane / 4.5 h / 0 - 20 °C

12.1: methanol; sodium hydroxide / water / 1 h / 0 °C / Inert atmosphere

With 4-methyl-morpholine; methanol; dmap; lithium borohydride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

acetic acid 3S-{5R-(3'-{4S-acetoxy-1-[2S-(2S-methylaminopropionylamino)butyryl]pyrrolidin-2R-ylmethyl}-6,6'-difluoro-1H,1'H-[2,2']biindol-3-ylmethyl)-1-[2S-(2S-methylaminopropionylamino)butyryl]pyrrolidin}-3-yl ester

(2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(6-fluoro-1H-indole-3-carbonyl)pyrrolidine-1-carboxylic acid benzyl ester

(2S,4R)-2-(6-fluoro-1H-indol-3-carbonyl)-4-hydroxypyrrolidine-1-carboxylic acid benzyl ester

[2S-(6-fluoro-1H-indole-3-carbonyl)-4S-(4'-nitrobenzoyloxy)pyrrolidin-1-yl]carboxylic acid benzyl ester

Refernces

• 1、 -. "SMAC MIMETIC (BIRINAPANT) FOR USE IN THE TREATMENT OF PROLIFERATIVE DISEASES (CANCER)". Paragraph 0074; 0075; 0076. . Retrieved 2013/04/13.