tert-butyl (1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate

Base Information

• Chemical Name: tert-butyl (1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate
• CAS No.: 1310731-06-6
• Molecular Formula: C₂₄H₃₀N₆O₅S
• Molecular Weight: 514.605
• Mol file: 1310731-06-6.mol

Synonyms:

Chemical Property of tert-butyl (1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate

There total 5 articles about tert-butyl (1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate 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:

2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (1201186-57-3) + (1R,3R)-3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid (489446-85-7) → tert-butyl (1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate (1310731-06-6)

Guidance literature:

With hydrogenchloride; 1,2-dichloro-ethane; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1016/j.bmcl.2015.09.020

Reference yield:

5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine (875781-41-2) → tert-butyl (1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate (1310731-06-6)

Guidance literature:

Multi-step reaction with 4 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 / tert-Amyl alcohol; 1,4-dioxane / 2 h / 95 °C

3: phosphoric acid / tetrahydrofuran; n-heptane / 2 h / 70 °C

4: hydrogenchloride; 1,2-dichloro-ethane / dichloromethane / 15 h / 20 °C

With hydrogenchloride; phosphoric acid; palladium diacetate; sodium hydride; potassium carbonate; 1,2-dichloro-ethane; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; tert-Amyl alcohol; n-heptane; dichloromethane; N,N-dimethyl-formamide; 2: |Buchwald-Hartwig Coupling;

DOI:10.1016/j.bmcl.2015.09.020

Reference yield:

2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine (1201186-54-0) → tert-butyl (1R,3R)-3-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)cyclopentylcarbamate (1310731-06-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2: phosphoric acid / tetrahydrofuran; n-heptane / 2 h / 70 °C

3: hydrogenchloride; 1,2-dichloro-ethane / dichloromethane / 15 h / 20 °C

With hydrogenchloride; phosphoric acid; palladium diacetate; potassium carbonate; 1,2-dichloro-ethane; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; tert-Amyl alcohol; n-heptane; dichloromethane; 1: |Buchwald-Hartwig Coupling;

DOI:10.1016/j.bmcl.2015.09.020

upstream raw materials:

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

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

C₂₃H₂₉N₅O₆S

2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine