tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate

Base Information

Chemical Name:tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate
CAS No.:1210419-95-6
Molecular Formula:C₂₉H₃₁F₃N₄O₄
Molecular Weight:556.585
Hs Code.:

Synonyms:tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate

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Chemical Property of tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate

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Technology Process of tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate

There total 19 articles about tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate 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: 99.0%

: 1210419-19-4
6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxylic acid

: (1R,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-((tert-butoxycarbonyl)amino)-6-methylcyclohexyl acetate

: 1210419-95-6
tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate

Guidance literature:: 6-(2,6-difluorophenyl)-5-fluoropyridine-2-carboxylic acid; (1R,2R,4R,6S)-4-(3-aminopyridin-4-yl)-2-((tert-butoxycarbonyl)amino)-6-methylcyclohexyl acetate; With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; N,N-dimethyl-formamide; at 20 ℃; for 6h;

With caesium carbonate; In ethanol; at 60 ℃; for 1.5h;

Reference yield:

: 374633-36-0
2-bromo-3-fluoro-6-methylpyridine

: 1210419-95-6
tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tri-tert-butyl phosphine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium fluoride / water; tetrahydrofuran / 1 h / 60 °C / Inert atmosphere

1.2: 1 h / 20 °C

2.1: potassium permanganate / water / Reflux

3.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; ethanol / 6 h / 20 °C

3.2: 1.5 h / 60 °C

With potassium fluoride; potassium permanganate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1-hydroxy-7-aza-benzotriazole; tri-tert-butyl phosphine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

Reference yield:

: 1187055-93-1
5-methyl-3-oxocyclohex-1-en-1-yl trifluoromethanesulfonate

: 1210419-95-6
tert-butyl (1R,2R,3S,5R)-5-(3-(6-(2,6-difluorophenyl)-5-fluoropicolinamido)pyridin-4-yl)-2-hydroxy-3-methylcyclohexylcarbamate

Guidance literature:: Multi-step reaction with 11 steps

1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 10 h / 80 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / water; 1,4-dioxane / 1 h / 110 °C / Reflux

3.1: ethanol; sodium tetrahydroborate; cerium(III) chloride heptahydrate / 1 h / 0 °C

4.1: toluene-4-sulfonic acid / 1,4-dioxane / 3 h / 100 °C

5.1: N-Bromosuccinimide / water; tetrahydrofuran / 0.5 h / 20 °C

6.1: potassium tert-butylate / tetrahydrofuran / 0.5 h

6.2: 20 °C

7.1: ammonium hydroxide; trimethylphosphane / pyridine / 2 h / 20 °C

7.2: 2 h / 20 °C

8.1: pyridine / 20 °C

9.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 72 h / 20 °C

10.1: AD-H chiral column / isopropyl alcohol; n-heptane / Resolution of racemate

11.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; ethanol / 6 h / 20 °C

11.2: 1.5 h / 60 °C

With pyridine; ammonium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; 1-hydroxy-7-aza-benzotriazole; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ethanol; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; potassium acetate; sodium carbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; n-heptane; water; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;