4-(aminomethyl)-2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)benzamide

Base Information

• Chemical Name: 4-(aminomethyl)-2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)benzamide
• CAS No.: 1258295-35-0
• Molecular Formula: C₁₇H₁₆Cl₂N₄O₂
• Molecular Weight: 379.246
• Mol file: 1258295-35-0.mol

Synonyms:

Chemical Property of 4-(aminomethyl)-2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(aminomethyl)-2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)benzamide

There total 13 articles about 4-(aminomethyl)-2,6-dichloro-N-(2-(cyclopropanecarboxamido)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: 16.0%

2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide (1258298-20-2) → 4-(aminomethyl)-2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)benzamide (1258295-35-0)

Guidance literature:

With ammonia; hydrogen; In ethanol; at 20 ℃; for 24h;

DOI:10.1021/jm400266t

Reference yield:

trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-2,6-dichloro-phenyl ester (1098619-84-1) → 4-(aminomethyl)-2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)benzamide (1258295-35-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: palladium diacetate; triethylamine; 1,3-bis-(diphenylphosphino)propane / N,N-dimethyl-formamide / 7600.51 Torr

2.1: sulfuric acid / ethyl acetate / 2 h / 20 °C

3.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -5 - 0 °C

3.2: 20 °C

4.1: pyridine; lithium iodide / water / 30 h / 130 °C

5.1: thionyl chloride / Reflux; Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

6.2: 12 h / 0 - 25 °C / Inert atmosphere

7.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere

8.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 2 h / 140 °C / Sealed tube; Inert atmosphere; Microwave irradiation

9.1: ozone / dichloromethane; methanol / -78 °C

9.2: -78 °C / Inert atmosphere

10.1: hydrogen; ammonia / ethanol / 24 h / 20 °C

With pyridine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; sulfuric acid; 1,3-bis-(diphenylphosphino)propane; ammonia; hydrogen; palladium diacetate; sodium hydride; sodium carbonate; caesium carbonate; ozone; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium iodide; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm400266t

Reference yield:

methyl 4-amino-2,6-dichlorobenzoate (232275-49-9) → 4-(aminomethyl)-2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)benzamide (1258295-35-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / -5 - 0 °C

1.2: 20 °C

2.1: pyridine; lithium iodide / water / 30 h / 130 °C

3.1: thionyl chloride / Reflux; Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

4.2: 12 h / 0 - 25 °C / Inert atmosphere

5.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere

6.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 2 h / 140 °C / Sealed tube; Inert atmosphere; Microwave irradiation

7.1: ozone / dichloromethane; methanol / -78 °C

7.2: -78 °C / Inert atmosphere

8.1: hydrogen; ammonia / ethanol / 24 h / 20 °C

With pyridine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; ammonia; hydrogen; sodium hydride; sodium carbonate; caesium carbonate; ozone; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium iodide; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm400266t

upstream raw materials:

trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-2,6-dichloro-phenyl ester

methyl 4-amino-2,6-dichlorobenzoate

2,6-dichloro-4-iodo-benzoic acid methyl ester

2,6-dichloro-4-iodo-benzoic acid