1022150-11-3

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 3-[4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-1-yl]-, 1,1-diMethylethyl ester, (3R)-
• Synonyms: 1-Piperidinecarboxylic acid, 3-[4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-1-yl]-, 1,1-diMethylethyl ester, (3R)-;(R)-tert-Butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate;(R)-tert-Butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (N-1);3-[4-Amino-3-(4-phenoxy-phenyl)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester;Ibrutinib Intermediates;(R)-tert-Butyl 3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-ca
• CAS NO: 1022150-11-3
• Molecular Formula: C₂₇H₃₀N₆O₃
• Molecular Weight: 486.5655
• Mol File: 1022150-11-3.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 673.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.09±0.30(Predicted)
• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 3-[4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-1-yl]-, 1,1-diMethylethyl ester, (3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 3-[4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-1-yl]-, 1,1-diMethylethyl ester, (3R)-(1022150-11-3)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 3-[4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-1-yl]-, 1,1-diMethylethyl ester, (3R)-(1022150-11-3)

Safety Data

• Hazardous Substances Data: 1022150-11-3(Hazardous Substances Data)

Usage

Description

1-Piperidinecarboxylic acid, 3-[4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-1-yl]-, 1,1-diMethylethyl ester, (3R)is a pyrazolopyrimidine compound with the molecular formula C27H33N7O2. It is an isomer of the drug Tadalafil and is known for its specific 3D molecular structure and stereochemistry, which are crucial for its biological activity and pharmacological properties. This chemical is commonly utilized in the synthesis of pharmaceutical products.

Uses

Used in Pharmaceutical Industry:
1-Piperidinecarboxylic acid, 3-[4-aMino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyriMidin-1-yl]-, 1,1-diMethylethyl ester, (3R)is used as an intermediate in the synthesis of pharmaceutical products for its potential applications in the treatment of erectile dysfunction and pulmonary arterial hypertension. Its unique molecular structure and stereochemistry contribute to its effectiveness in these therapeutic areas.

Upstream product

• 330786-24-8 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 143900-44-1 tert-butyl (3S)-3-hydroxypiperidine-1-carboxylate 
• 1353993-49-3 tert-butyl (3S)-3-[[(4-methylbenzene)sulfonyl]oxy]piperidine-1-carboxylate 
• 2215-77-2 4-Phenoxybenzoic acid 
• 330792-68-2 2-[hydroxy-(4-phenoxy-phenyl)-methylene]-malononitrile 
• 108-95-2 phenol 
• 459-57-4 4-fluorobenzaldehyde 
• 330792-69-3 2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile 
• 1419223-01-0 tert-butyl (3R)-3-(4-amino-3-bromo-1H-pyrazolo [3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate 
• 51067-38-0 4-phenoxyphenylboronic acid 
• 83255-86-1 3-bromo-4-aminopyrazolo<3,4-d>pyrimidine 
• 940890-90-4 (S)-3-methanesulfonyloxy-piperidine-1-carboxylic acid tert-butyl ester 
• 143900-43-0 tert-butyl (3R)-3-hydroxypiperidine-1-carboxylate 
• 1623-95-6 4-phenoxybenzoyl chloride 

Downstream Products

• 1022150-12-4 (R)-3-(4-phenoxyphenyl)-1-(piperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine-4-amine 
• 1412418-18-8 (R)-2-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-3-cyclopropylacrylonitrile 
• 1412418-65-5 _{(R)-2-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4,4-dimethylpent-2-enenitrile} 
• 1710768-30-1 (R,E)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]-pyrimidin-1-yl)piperidin-1-yl)-4-(4-(2-aminoethyl)piperazin-1-yl)but-2-en-1-one 
• 936563-87-0 ibrutinib 
• 1642571-07-0 (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride 

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.

A PROCESS FOR PREPARATION OF 1H-PYRAZOLO[3,4-D] PYRIMIDINE DERIVATIVES

The present invention relates to an efficient and industrially advantageous process for the preparation of 1H-pyrazolo[3,4-d] pyrimidine derivatives. In particular the present invention provides a process for the preparation of 4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4- d]pyrimidine and tert-butyl (R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4- d]pyrimidin-1-yl)piperidine-1-carboxylate. Said compounds are important intermediates in the synthesis of ibrutinib. The method provided for preparing intermediates of ibrutinib has the advantages of a simple operation, high yield and low costs.

Method for using zinc chloride to separate and purify ibrutinib intermediate

The invention discloses a method for using zinc chloride to separate and purify an ibrutinib intermediate, and particularly relates to a separation and purification method of the ibrutinib intermediate (3R)-4-amido-3-(4-phenoxy phenyl)-1-(1-tert-butoxy carbonyl piperidine-3-yl)-1H-pyrazolo[3,4-d]pyrimidine. After Mitsunobu reaction for preparing the intermediate is terminated, zinc chloride is added into a mixture, heated and cooled, composition sediment of zinc chloride and triphenylphosphine oxide is removed by filtering, and the intermediate with good purity is obtained. The process omits column chromatography, and is an efficient and low-cost separation and purification method.