2-Pyrazinecarboxamide, N,N',N''-[2,4,6-boroxintriyltris[[(1R)-3-methylbutylidene]imino[(1S)-2-oxo-1-(phenylmethyl)-2,1-ethanediyl]]]tris-

Base Information

• Chemical Name: 2-Pyrazinecarboxamide, N,N',N''-[2,4,6-boroxintriyltris[[(1R)-3-methylbutylidene]imino[(1S)-2-oxo-1-(phenylmethyl)-2,1-ethanediyl]]]tris-
• CAS No.: 390800-88-1
• Molecular Formula: C57H69B3N12O9
• Molecular Weight: 1098.68
• Mol file: 390800-88-1.mol

Synonyms:Pyrazinecarboxamide, N,N',N''-[2,4,6-boroxintriyltris[[(1R)-3-methylbutylidene]imino[(1S)-2-oxo-1-(phenylmethyl)-2,1-ethanediyl]]]tris- (9CI);

Chemical Property of 2-Pyrazinecarboxamide, N,N',N''-[2,4,6-boroxintriyltris[[(1R)-3-methylbutylidene]imino[(1S)-2-oxo-1-(phenylmethyl)-2,1-ethanediyl]]]tris-

Chemical Property:

• Boiling Point: 1277.7±65.0 °C(Predicted)
• PKA: 11.46±0.46(Predicted)
• PSA: 279.63000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 7.82370
• Storage Temp.: -20°C Freezer

Purity/Quality:

98%,99%, ^*data from raw suppliers

BortezomibTrimer ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Bortezomib Trimer is derived from Bortezomib (B675700), which is the first proteasome inhibitor to be approved by the US FDA for multiple myeloma, a blood cancer. A reversible inhibitor of the 26S proteasome-a barrel-shaped multiprotein particle found in the nucleus and cytosol of all eukaryotic cells. Targets the ubiquitin-proteasome pathway.

Technology Process of 2-Pyrazinecarboxamide, N,N',N''-[2,4,6-boroxintriyltris[[(1R)-3-methylbutylidene]imino[(1S)-2-oxo-1-(phenylmethyl)-2,1-ethanediyl]]]tris-

There total 4 articles about 2-Pyrazinecarboxamide, N,N',N''-[2,4,6-boroxintriyltris[[(1R)-3-methylbutylidene]imino[(1S)-2-oxo-1-(phenylmethyl)-2,1-ethanediyl]]]tris- 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: 83.0%

N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide (205393-22-2) + (1S,2S,3R,5S)-pinanediol N-(2-pyrazinecarbonyl)-L-phenylalanine-L-leucine boronate → bortezomib (390800-88-1) + N-(2-pyrazinecarbonyl)-L-phenylalanine-L-leucine boronic anhydride

Guidance literature:

With Dihydroxy-isobutyl-boran; In methanol; n-heptane; water; at 21.6 - 28.6 ℃; for 16.38h; Product distribution / selectivity; Industry scale;

Reference yield: 80.0%

N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide (205393-22-2) → bortezomib (390800-88-1)

Guidance literature:

With hydrogenchloride; Dihydroxy-isobutyl-boran; In methanol; hexane;

Reference yield: 76.9%

velcade (179324-69-7,1132709-16-0) → bortezomib (390800-88-1)

Guidance literature:

In isopropyl alcohol; acetonitrile; at 20 ℃; for 4h; Product distribution / selectivity;

upstream raw materials:

N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

velcade

Downstream raw materials:

2-((R)-2-((R)-3-methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)-5-oxo-1,3,2-dioxaborolan-4-yl)acetic acid

N-((S)-1-((R)-3-methyl-1-(4-oxo-4H-benzo[d][1,3,2]dioxaborinin-2-yl)butylamino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide

N-[(1S)-1-benzyl-2-({(1R)-3-methyl-1-[(5R)-4-oxo-5-phenyl-1,3,2-dioxaborolan-2-yl]butyl}amino)-2-oxoethyl]pyrazine-2-carboxamide

(S)-2-hydroxy-2-((S)-2-((R)-3-methyl-1-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)-5-oxo-1,3,2-dioxaborolan-4-yl)acetic acid

Refernces

• 1、 -. "METHODS FOR PREPARING BORTEZOMIB AND INTERMEDIATES USED IN ITS MANUFACTURE". Page/Page column 14. . Retrieved 2009/03/07.
• 2、 -. "SYNTHESIS OF BORONIC ESTER AND ACID COMPOUNDS". Page/Page column 48-50. . Retrieved 2010/02/14.