2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide

Base Information

• Chemical Name: 2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide
• CAS No.: 1196531-32-4
• Molecular Formula: C₁₉H₂₇N₅O₃
• Molecular Weight: 373.455
• Mol file: 1196531-32-4.mol

Synonyms:2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide

Chemical Property of 2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide

There total 6 articles about 2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide 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: 97.0%

2-[4-(4-amino-5-cyano-2-methoxy-phenoxy)-1-piperidyl]-N-methylacetamide (1196531-38-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide (1196531-32-4)

Guidance literature:

With acetic acid; In 2-methyltetrahydrofuran; at 76 ℃; for 16h;

Reference yield:

2-methoxy-5-cyanophenol (52805-46-6) → 2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide (1196531-32-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate / water / 60 - 100 °C / Inert atmosphere; Industrial scale

1.2: 97 - 103 °C / Inert atmosphere; Industrial scale

2.1: hydrogenchloride / isopropyl alcohol / 75 - 85 °C / Inert atmosphere; Industrial scale

3.1: triethanolamine / ethanol / 12 h / 80 - 81 °C / Inert atmosphere; Industrial scale

4.1: acetic acid; sulfuric acid; nitric acid / 42 - 48 °C / Inert atmosphere; Industrial scale

5.1: 1 % platinum and 2% vanadium on carbon / acetonitrile / 40 °C / Inert atmosphere; Industrial scale

5.2: 6 h / 40 °C / 2250.23 Torr / Industrial scale

6.1: toluene / Inert atmosphere

With hydrogenchloride; triethanolamine; sulfuric acid; 1 % platinum and 2% vanadium on carbon; nitric acid; potassium carbonate; acetic acid; In ethanol; water; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1021/acs.oprd.6b00412

Reference yield:

tert-butyl 4-(5-cyano-2-methoxy-phenoxy)piperidine-1-carboxylate (1196531-33-5) → 2-[4-(5-cyano-4-{[(dimethylamino)methylene]amino}-2-methoxyphenoxy)piperidin-1-yl]-N-methylacetamide (1196531-32-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogenchloride / isopropyl alcohol / 75 - 85 °C / Inert atmosphere; Industrial scale

2.1: triethanolamine / ethanol / 12 h / 80 - 81 °C / Inert atmosphere; Industrial scale

3.1: acetic acid; sulfuric acid; nitric acid / 42 - 48 °C / Inert atmosphere; Industrial scale

4.1: 1 % platinum and 2% vanadium on carbon / acetonitrile / 40 °C / Inert atmosphere; Industrial scale

4.2: 6 h / 40 °C / 2250.23 Torr / Industrial scale

5.1: toluene / Inert atmosphere

With hydrogenchloride; triethanolamine; sulfuric acid; 1 % platinum and 2% vanadium on carbon; nitric acid; acetic acid; In ethanol; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1021/acs.oprd.6b00412

upstream raw materials:

2-[4-(4-amino-5-cyano-2-methoxy-phenoxy)-1-piperidyl]-N-methylacetamide

N,N-dimethyl-formamide dimethyl acetal

2-methoxy-5-cyanophenol

tert-butyl 4-(5-cyano-2-methoxy-phenoxy)piperidine-1-carboxylate

Downstream raw materials:

Sapitinib