tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate
• CAS No.: 1201187-44-1
• Molecular Formula: C₁₈H₂₀N₄O₄S
• Molecular Weight: 388.447
• Mol file: 1201187-44-1.mol

Synonyms:N-(5-(p-toluenesulfonyl)pyrrolo[2,3-b]pyrazin-2-yl)carbamic acid tert-butyl ester

Chemical Property of tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate

Chemical Property:

• PKA: 9.45±0.43(Predicted)
• Density: 1.35±0.1 g/cm3(Predicted)

Purity/Quality:

99%, ^*data from raw suppliers

2-(Boc-amino)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: tert-Butyl N-[5-(4-methylbenzenesulfonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamate is a reagent in the synthetic preparation of tricyclic heterocycles and their kinase inhibitory activity. Preparation of novel nitrogen-containing tricyclic compounds as kinase inhibitors for treating immunological and oncological conditions.

Technology Process of tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate

There total 11 articles about tert-butyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate 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: 75.0%

tert-butyl carbazate (4248-19-5) + 2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine (1201186-54-0) → N-(5-(p-toluenesulfonyl)pyrrolo[2,3-b]pyrazin-2-yl)carbamic acid tert-butyl ester (1201187-44-1)

Guidance literature:

With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105 ℃; for 2.5h;

Reference yield: 54.0%

5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carboxylic acid + tert-butyl alcohol (75-65-0) → N-(5-(p-toluenesulfonyl)pyrrolo[2,3-b]pyrazin-2-yl)carbamic acid tert-butyl ester (1201187-44-1)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; at 70 ℃; for 16h;

Reference yield:

5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine (875781-41-2) → N-(5-(p-toluenesulfonyl)pyrrolo[2,3-b]pyrazin-2-yl)carbamic acid tert-butyl ester (1201187-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

2: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium carbonate / 1,4-dioxane; tert-Amyl alcohol / 3 h / 95 °C

With palladium diacetate; sodium hydride; potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; tert-Amyl alcohol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2012.11.108

upstream raw materials:

tert-butyl carbazate

2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine

5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine

tert-butyl alcohol

Downstream raw materials:

8-cyclohexyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine

8-cyclohexyl-3-tosyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine

C₂₁H₂₄N₄O₃S

(3R,4S)-benzyl 3-(2-(tert-butoxycarbonyl(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)-4-ethylpyrrolidine-1-carboxylate

Refernces

• 1、 Bhagavatula, Lakshmi,Christesen, Alan,Dunn, Travis B.,Ickes, Andrew,Kotecki, Brian J.,Marek, James C.,Morrill, Westin H.,Moschetta, Eric,Mulhern, Mathew,Rasmussen, Michael,Reynolds, Troy,Rozema, Michael J.,Yu, Su. "Development of a Scalable Enantioselective Synthesis of JAK Inhibitor Upadacitinib". . . Retrieved 2021/10/21.
• 2、 -. "Synthesis method of JAK (Janus Kinase) inhibitor". Paragraph 0083-0084. . Retrieved 2019/03/08.