1420478-89-2

Basic information

• Product Name: (S)-benzyl 2-(8-amino-1-(4-(pyridin-2-ylcarbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate
• Synonyms: (S)-benzyl 2-(8-amino-1-(4-(pyridin-2-ylcarbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate;(S)-2-{8-Amino-1-[4-(pyridin-2-ylcarbamoyl)-phenyl]-imidazo[1,5-a] pyrazin-3-yl}-pyrrolidine-1-carboxylic acid benzyl ester;1-Pyrrolidinecarboxylic acid, 2-[8-amino-1-[4-[(2-pyridinylamino)carbonyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]-, phenylmethyl ester, (2S)-
• CAS NO: 1420478-89-2
• Molecular Formula: C₃₀H₂₇N₇O₃
• Molecular Weight: 533.58048
• Mol File: 1420478-89-2.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• PKA: 11.47±0.70(Predicted)
• CAS DataBase Reference: (S)-benzyl 2-(8-amino-1-(4-(pyridin-2-ylcarbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-benzyl 2-(8-amino-1-(4-(pyridin-2-ylcarbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate(1420478-89-2)
• EPA Substance Registry System: (S)-benzyl 2-(8-amino-1-(4-(pyridin-2-ylcarbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate(1420478-89-2)

Safety Data

• Hazardous Substances Data: 1420478-89-2(Hazardous Substances Data)

Usage

General Description

(S)-benzyl 2-(8-amino-1-(4-(pyridin-2-ylcarbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate is a complex chemical compound with a unique molecular structure. It consists of a benzyl group attached to a pyrrolidine-1-carboxylate, which is further connected to a series of interconnected aromatic rings containing nitrogen and carbon atoms. (S)-benzyl 2-(8-amino-1-(4-(pyridin-2-ylcarbamoyl)phenyl)imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate possesses potential pharmacological properties and may have applications in medicinal chemistry, biochemistry, and drug development. Its precise molecular structure and properties would need to be further studied and investigated to fully understand its potential utility and effects.

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 61350-60-5 (S)-benzyloxycarbonyl-proline acid chloride 
• 300401-95-0 4-iodo-N-(pyridin-2-yl)benzamide 
• 1333433-59-2 (S)-benzyl 2-carbamimidoylpyrrolidine-1-carboxylate 
• 504-29-0 2-aminopyridine 
• 180516-87-4 4-carboxyphenylboronic acid pinacol ester 
• 14547-83-2 4-bromo-N-(pyridin-2-yl)benzamide 
• 586-75-4 4-chlorobenzoyl chloride 
• 1420478-88-1 benzyl (2S)-2-(8-amino-1-bromo-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate 
• 586-76-5 4-Bromobenzoic acid 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 1418307-17-1 benzyl (S)-2-(((3-chloropyrazin-2-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate 
• 850568-25-1 4-(pyridin-2-yl-aminocarbonyl)benzeneboronic acid 
• 1420478-87-0 benzyl (2S)-2-(1-bromo-8-chloro-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate 

Downstream Products

• 1420478-90-5 4-{8-amino-3-[(2S)-pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-N-(pyridin-2-yl)benzamide 
• 1420477-60-6 4-{8-amino-3-[(2S)-1-(1-oxo-2-butyn-1-yl)pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-N-(pyridin-2-yl)benzamide 

Relevant articles and documents

Method for preparing Acalabrutinib, in particular to method for preparing Acalabrutinib

The invention relates to the field of chemical synthesis, in particular to a chemical synthesis method for preparing Acalabrutinib. The synthesis method of the compound 3 is optimized, wherein the cyano compound 2 is reduced to obtain the compound 3 by adopting a method of generating borane in situ under the conditions of indium trichloride and sodium borohydride. The method is simple and convenient to operate, a special reaction container and hydrogen are not needed for reduction, a high-risk material catalyst nickel is prevented from being adopted, and large-scale production is facilitated.In the preparation of the compound 15, water is used as a solvent, equivalent hydrogen peroxide is added to react the compound 13 with the compound 14 to prepare the compound 15, so that the method iseconomic and environment-friendly, the post-treatment is simple and convenient, and the reaction liquid is directly subjected to centrifugal operation; in addition, the yield is high and can reach 90% or above; and the compound 15 is high in purity and does not need to be further purified, so that the technology can satisfy the requirements of industrial production.

PROCESS FOR THE PREPARATION OF ACALABRUTINIB AND ITS INTERMEDIATES

The present invention provides an improved and industrially viable process for the preparation of Acalabrutinib and its intermediates in high yield and eliminating the use of time-consuming purification process. The present invention also relates to the purification of (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-alpyrazin-1-yl)-N-(pyridin-2-yl) benzamide, a key intermediate for the preparation of Acalabrutinib. Further present invention relates to new polymorphic form of Acalabrutinib.

Acalabrutinib and its intermediate synthesis method (by machine translation)

The invention discloses a method for synthesizing Acalabrutinib, including proline derivatives of formula L - 1 and 2 - chloro - 2 - formyl acetonitrile as the starting material by direct condensation and cyclization of formula 2, after the bromo acetal with low-cost [...] methanol intermediate obtained by reaction of formula 3, followed by hydrolysis, cyclization reaction to obtain the key intermediate of formula 6, then with the borate intermediates of formula 8 to Suzuki coupling, then deprotected and get of formula 10, finally with the final product is obtained butynoic acid condensation Acalabrutinib type 11. The route the operation is simple, not only higher total yield, purity of the obtained products is also high, and suitable for production. (by machine translation)