2,6-dichloro-4-cyano-N-(2-(1R,2R)-(2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide

Base Information

• Chemical Name: 2,6-dichloro-4-cyano-N-(2-(1R,2R)-(2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide
• CAS No.: 1258294-31-3
• Molecular Formula: C₁₇H₁₁Cl₂FN₄O₂
• Molecular Weight: 393.204
• Mol file: 1258294-31-3.mol

Synonyms:2,6-dichloro-4-cyano-N-(2-(1R,2R)-(2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide

Chemical Property of 2,6-dichloro-4-cyano-N-(2-(1R,2R)-(2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-dichloro-4-cyano-N-(2-(1R,2R)-(2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide

There total 11 articles about 2,6-dichloro-4-cyano-N-(2-(1R,2R)-(2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide 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: 6.4%

C17H11Cl2FN4O2 → 2,6-dichloro-4-cyano-N-(2-(1R,2R)-(2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide (1258294-31-3) + 2,6-dichloro-4-cyano-N-(2-((1S,2S)-2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide (1258294-30-2)

Guidance literature:

With Chiralpak IC; In methanol; for 0.0833333h; Resolution of racemate;

DOI:10.1021/jm400266t

Reference yield:

N-(2-bromopyridin-4-yl)-2,6-dichloro-4-cyanobenzamide (1258298-07-5) + cis-2-fluorocyclopropanecarboxamide → 2,6-dichloro-4-cyano-N-(2-(1R,2R)-(2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide (1258294-31-3) + 2,6-dichloro-4-cyano-N-(2-((1S,2S)-2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide (1258294-30-2)

Guidance literature:

With caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 140 ℃; for 1h; Microwave irradiation; Inert atmosphere;

Reference yield:

dimethyl aminoterephthalate (5372-81-6) → 2,6-dichloro-4-cyano-N-(2-(1R,2R)-(2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide (1258294-31-3) + 2,6-dichloro-4-cyano-N-(2-((1S,2S)-2-fluorocyclopropanecarboxamido)pyridin-4-yl)benzamide (1258294-30-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrachloromethane; N-chloro-succinimide / 16 h / 80 °C

2.1: isopentyl nitrite / tetrahydrofuran / 3 h / 20 °C / Reflux

3.1: water; sodium hydroxide / tetrahydrofuran / 48 h / 20 °C

4.1: triethylamine / tetrahydrofuran / 0.33 h / 20 °C

4.2: 18 h / 20 °C

5.1: pyridine; trifluoroacetic anhydride / 1,4-dioxane / 24 h / 20 °C

6.1: pyridine; lithium iodide / 2 h / 20 °C / Reflux

7.1: thionyl chloride / Reflux; Inert atmosphere

8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C

8.2: 1 h / 20 °C / Inert atmosphere

9.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 1 h / 140 °C / Inert atmosphere; Sealed tube; Microwave irradiation

10.1: Chiralpak IC / methanol / 0.08 h / Resolution of racemate

With pyridine; tetrachloromethane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-chloro-succinimide; thionyl chloride; water; sodium hydride; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic anhydride; sodium hydroxide; lithium iodide; isopentyl nitrite; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm400266t

upstream raw materials:

N-(2-bromopyridin-4-yl)-2,6-dichloro-4-cyanobenzamide

dimethyl aminoterephthalate

2-amino-3,5-dichloro-4-(carbomethoxy)benzoic acid methyl ester

dimethyl 2,6-dichlorobenzene-1,4-dicarboxylate