1642571-07-0

Basic information

• Product Name: (S)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• Synonyms: Ibrutinib iMpurity SYGIM HCl
• CAS NO: 1642571-07-0
• Molecular Formula: C22H22N6O
• Molecular Weight: 386.44968
• Mol File: 1642571-07-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine(1642571-07-0)
• EPA Substance Registry System: (S)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine(1642571-07-0)

Safety Data

• Hazardous Substances Data: 1642571-07-0(Hazardous Substances Data)

Upstream product

• 940890-90-4 (S)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester 
• 330786-24-8 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 330792-69-3 2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile 
• 330792-68-2 2-[hydroxy-(4-phenoxy-phenyl)-methylene]-malononitrile 
• 1623-95-6 4-phenoxybenzoyl chloride 
• 2215-77-2 4-Phenoxybenzoic acid 
• 83255-86-1 3-bromo-4-aminopyrazolo<3,4-d>pyrimidine 
• 51067-38-0 4-phenoxyphenylboronic acid 
• 1419223-01-0 tert-butyl (3R)-3-(4-amino-3-bromo-1H-pyrazolo [3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate 
• 1276110-38-3 (R)-3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylic acid tert-butyl ester 
• 143900-44-1 tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate 
• 936563-86-9 tert-butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate 
• 151266-23-8 4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidine 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 1553977-08-4 (R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-2,3,3-d₃-1-one 
• 936563-87-0 ibrutinib 

Relevant articles and documents

Tumor-Cell-Specific Targeting of Ibrutinib: Introducing Electrostatic Antibody-Inhibitor Conjugates (AiCs)

Ibrutinib is an inhibitor of Bruton's tyrosine kinase that has been approved for the treatment of patients with chronic lymphocytic leukemia, mantle cell lymphoma and Waldenstrom's macroglobulinemia and is connected with toxicities. To minimize its toxicities, we linked ibrutinib to a cell-targeted, internalizing antibody. To this end, we synthesized a poly-anionic derivate, ibrutinib-Cy3.5, that retains full functionality. This anionic inhibitor is complexed by our anti-CD20-protamine targeting conjugate and free protamine, and thereby spontaneously assembles into an electrostatically stabilized vesicular nanocarrier. The complexation led to an accumulation of the drug driven by the CD20 antigen internalization to the intended cells and an amplification of its pharmacological effectivity. In vivo, we observed a significant enrichment of the drug in xenograft lymphoma tumors in immune-compromised mice and a significantly better response to lower doses compared to the original drug.

AN IMPROVED PROCESS FOR THE PREPARATION OF IBRUTINIB

The present invention relates to an improved process for the preparation of Ibrutinib with high purity and high yields. The present process is cost effective and feasible in large scale production also. The present process avoids the mitsunobu reagent conditions also. The present Invention also relates to a process for the preparation of Crystalline form A and Crystalline form C of Ibrutinib.

PROCESS FOR THE PREPARATION OF IBRUTINIB AND NEW SYNTHESIS INTERMEDIATE

Subject-matter of the invention is a process for the preparation of ibrutinib and intermediate compound.