5-{6-[tert-butoxycarbonyl-(3-methoxyphenyl)amino]pyrazin-2-yl}nicotinic acid

Base Information

Chemical Name:5-{6-[tert-butoxycarbonyl-(3-methoxyphenyl)amino]pyrazin-2-yl}nicotinic acid
CAS No.:405940-21-8
Molecular Formula:C₂₂H₂₂N₄O₅
Molecular Weight:422.44
Hs Code.:

Synonyms:5-{6-[tert-butoxycarbonyl-(3-methoxyphenyl)amino]pyrazin-2-yl}nicotinic acid

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Chemical Property of 5-{6-[tert-butoxycarbonyl-(3-methoxyphenyl)amino]pyrazin-2-yl}nicotinic acid

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Technology Process of 5-{6-[tert-butoxycarbonyl-(3-methoxyphenyl)amino]pyrazin-2-yl}nicotinic acid

There total 5 articles about 5-{6-[tert-butoxycarbonyl-(3-methoxyphenyl)amino]pyrazin-2-yl}nicotinic acid 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:

: 405940-20-7
5-{6-[tert-butoxycarbonyl-(3-methoxy-phenyl)-amino]-pyrazin-2-yl}-nicotinic acid ethyl ester

: 405940-21-8
5-{6-[tert-butoxycarbonyl-(3-methoxyphenyl)amino]pyrazin-2-yl}nicotinic acid

Guidance literature:: With sodium hydroxide; In methanol; at 0 - 20 ℃; for 18.3h;
DOI:10.1021/jm058205b

Reference yield:

: 20986-40-7
ethyl 5-bromo-3-pyridinecarboxylate

: 405940-21-8
5-{6-[tert-butoxycarbonyl-(3-methoxyphenyl)amino]pyrazin-2-yl}nicotinic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: bis(tributyltin); tri-o-tolylphosphine; triethylamine / palladium acetate / acetonitrile / 22 h / 95 - 100 °C

1.2: 3.56 g / dichloro-bis(triphenylphosphine)palladium; LiCl / toluene / 23 h / 100 °C

2.1: 65 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾*CHCl₃; 1,1'-bis(diphenylphosphino)ferrocene; Cs₂CO₃ / dioxane / 46 h / 110 °C

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

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

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; sodium hydroxide; bis(tri-n-butyltin); caesium carbonate; triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In 1,4-dioxane; methanol; dichloromethane; acetonitrile; 1.2: Stille coupling;
DOI:10.1021/jm058205b

Reference yield:

: 405938-99-0
5-(6-chloropyrazine-2-yl)nicotinic acid ethyl ester

: 405940-21-8
5-{6-[tert-butoxycarbonyl-(3-methoxyphenyl)amino]pyrazin-2-yl}nicotinic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 65 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾*CHCl₃; 1,1'-bis(diphenylphosphino)ferrocene; Cs₂CO₃ / dioxane / 46 h / 110 °C

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

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

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene; sodium hydroxide; caesium carbonate; In 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/jm058205b