1-Pyrrolidinecarboxylic acid, 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-, phenylmethyl ester, (2S)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-, phenylmethyl ester, (2S)-
• CAS No.: 1420478-88-1
• Molecular Formula: C18H18BrN5O2
• Molecular Weight: 416.277
• Mol file: 1420478-88-1.mol

Synonyms:1-Pyrrolidinecarboxylic acid, 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-, phenylmethyl ester, (2S)-;benzyl (S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate;(S)-benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate;benzyl (2S)-2-{8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl}pyrrolidine-1-carboxylate;S)-2-(8-Amino-1-bromo-imidazo[1,5-a]pyrazin-3-yl)-pyrrolidine -1-carboxylic acid benzyl ester;(2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-, phenylmethyl ester, (2S)-

Chemical Property:

• PKA: 4.67±0.30(Predicted)
• PSA: 85.75000
• Density: 1 +-.0.1 g/cm3(Predicted)
• LogP: 4.06680
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99.00% ^*data from raw suppliers

(S)-Benzyl2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S)-2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-1-Pyrrolidinecarboxylic acid phenylmethyl ester is used to Acalabrutinib intermediate.

Technology Process of 1-Pyrrolidinecarboxylic acid, 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-, phenylmethyl ester, (2S)-

There total 14 articles about 1-Pyrrolidinecarboxylic acid, 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)-, phenylmethyl ester, (2S)- 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: 87.0%

benzyl (2S)-2-(1-bromo-8-chloro-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (1420478-87-0) → benzyl (2S)-2-(8-amino-1-bromo-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (1420478-88-1)

Guidance literature:

With ammonium hydroxide; In isopropyl alcohol; at 90 ℃; for 14h; Sealed tube;

Reference yield:

C18H17BrN4O3 → benzyl (2S)-2-(8-amino-1-bromo-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (1420478-88-1)

Guidance literature:

With ammonium acetate; Reflux;

Reference yield:

benzyl (S)-2-(((3-chloropyrazin-2-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate (1418307-17-1) → benzyl (2S)-2-(8-amino-1-bromo-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (1420478-88-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,3-dimethyl-2-imidazolidinone; trichlorophosphate / acetonitrile / 0 - 65 °C

2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 20 °C

3: ammonia / isopropyl alcohol / -78 - 110 °C / 3000.3 - 3375.34 Torr

With 1,3-dimethyl-2-imidazolidinone; N-Bromosuccinimide; ammonia; trichlorophosphate; In N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

upstream raw materials:

(S)-2-(8-chloroimidazo[1,5-a]pyrazin-3-yl)-1-pyrrolidinecarboxylic acid benzyl ester

benzyl (2S)-2-(1-bromo-8-chloro-imidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate

benzyl (S)-2-(((3-chloropyrazin-2-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate

N-Benzyloxycarbonyl-L-proline

Downstream raw materials:

4-{8-amino-3-[(2S)-pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-N-(pyridin-2-yl)benzamide

(S,E)-4-(8-amino-3-(1-(4-(pyrrolidin-1-yl)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide

(S)-2-((1-(4-(pyridin-2-ylcarbamoyl)phenyl)-8-amino)imidazole[1,5-a]pyrazin-2-yl)pyrrolidine1-yl-carboxylic acid benzyl ester

(S)-4-(3-(1-Acryloylpyrrolidin-2-yl)-8-aminoimidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide

Refernces

• 1、 -. "Preparation method capable of acalabrutinib being used for treating leukemia". . . Retrieved 2020/07/24.
• 2、 -. "PROCESSES TO PRODUCE ACALABRUTINIB". . . Retrieved 2019/05/22.