[6-(5-tert-butoxycarbonylaminopyridin-3-yl)pyrazin-2-yl]-(4-chlorophenyl)carbamic acid tert-butyl ester

Base Information

• Chemical Name: [6-(5-tert-butoxycarbonylaminopyridin-3-yl)pyrazin-2-yl]-(4-chlorophenyl)carbamic acid tert-butyl ester
• CAS No.: 405939-08-4
• Molecular Formula: C₂₅H₂₈ClN₅O₄
• Molecular Weight: 497.981

Synonyms:[6-(5-tert-butoxycarbonylaminopyridin-3-yl)pyrazin-2-yl]-(4-chlorophenyl)carbamic acid tert-butyl ester

Chemical Property of [6-(5-tert-butoxycarbonylaminopyridin-3-yl)pyrazin-2-yl]-(4-chlorophenyl)carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of [6-(5-tert-butoxycarbonylaminopyridin-3-yl)pyrazin-2-yl]-(4-chlorophenyl)carbamic acid tert-butyl ester

There total 2 articles about [6-(5-tert-butoxycarbonylaminopyridin-3-yl)pyrazin-2-yl]-(4-chlorophenyl)carbamic acid tert-butyl ester 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:

5-{6-[tert-butoxycarbonyl-(4-chloro-phenyl)-amino]-pyrazin-2-yl}-nicotinic acid ethyl ester (405939-07-3) → [6-(5-tert-butoxycarbonylaminopyridin-3-yl)pyrazin-2-yl]-(4-chlorophenyl)carbamic acid tert-butyl ester (405939-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol / 18.3 h / 0 - 20 °C

2: 55 percent / diphenylphosphoryl azide; triethylamine / toluene / 4.5 h / 70 - 100 °C

With sodium hydroxide; diphenylphosphoranyl azide; triethylamine; In methanol; toluene; 2: Curtius rearrangement;

DOI:10.1021/jm058205b

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → [6-(5-tert-butoxycarbonylaminopyridin-3-yl)pyrazin-2-yl]-(4-chlorophenyl)carbamic acid tert-butyl ester (405939-08-4)

Guidance literature:

Multi-step reaction with 3 steps

1: (dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

2: aq. NaOH / methanol / 18.3 h / 0 - 20 °C

3: 55 percent / diphenylphosphoryl azide; triethylamine / toluene / 4.5 h / 70 - 100 °C

With dmap; sodium hydroxide; diphenylphosphoranyl azide; triethylamine; In methanol; dichloromethane; toluene; 3: Curtius rearrangement;

DOI:10.1021/jm058205b

Reference yield:

[6-(5-tert-butoxycarbonylaminopyridin-3-yl)pyrazin-2-yl]-(4-chlorophenyl)carbamic acid tert-butyl ester (405939-08-4) + 3-(4-pyridyl)-1-chloropropane (5264-02-8) → (6-{5-[tert-butoxycarbonyl-(3-pyridin-4-yl-propyl)-amino]-pyridin-3-yl}-pyrazin-2-yl)-(4-chloro-phenyl)-carbamic acid tert-butyl ester (405939-75-5)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 20h;

DOI:10.1021/jm058205b

upstream raw materials:

5-{6-[tert-butoxycarbonyl-(4-chloro-phenyl)-amino]-pyrazin-2-yl}-nicotinic acid ethyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

(6-{5-[tert-butoxycarbonyl-(3-pyridin-4-yl-propyl)-amino]-pyridin-3-yl}-pyrazin-2-yl)-(4-chloro-phenyl)-carbamic acid tert-butyl ester

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