2-(2-{[5-(2,6-dichloro-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-N-(2-hydroxy-ethyl)-acetamide

Base Information

• Chemical Name: 2-(2-{[5-(2,6-dichloro-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-N-(2-hydroxy-ethyl)-acetamide
• CAS No.: 1203603-94-4
• Molecular Formula: C₂₁H₁₈Cl₂N₆O₃S
• Molecular Weight: 505.384

Synonyms:2-(2-{[5-(2,6-dichloro-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-N-(2-hydroxy-ethyl)-acetamide

Chemical Property of 2-(2-{[5-(2,6-dichloro-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-N-(2-hydroxy-ethyl)-acetamide

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Technology Process of 2-(2-{[5-(2,6-dichloro-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-N-(2-hydroxy-ethyl)-acetamide

There total 12 articles about 2-(2-{[5-(2,6-dichloro-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-N-(2-hydroxy-ethyl)-acetamide 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: 31.0%

{[2-({[5-(2,6-dichlorophenyl)-1,2,4-triazin-3-yl]amino}methyl)-1,3-benzothiazol-5-yl]oxy}acetic acid (1203603-93-3) + ethanolamine (141-43-5) → 2-(2-{[5-(2,6-dichloro-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-N-(2-hydroxy-ethyl)-acetamide (1203603-94-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; at 20 - 50 ℃; Inert atmosphere;

Reference yield:

5-methoxybenzothiazole-2-carboxaldehyde (854059-90-8) → 2-(2-{[5-(2,6-dichloro-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-N-(2-hydroxy-ethyl)-acetamide (1203603-94-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium methylate; hydroxylamine hydrochloride / ethanol / 20 °C / Inert atmosphere

2.1: acetic acid; zinc / 3 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 50 - 85 °C / Inert atmosphere

4.1: boron tribromide / dichloromethane / 18 h / -78 - 20 °C / Inert atmosphere

5.1: potassium carbonate / acetone / 0.5 h / 20 °C / Inert atmosphere

5.2: 60 °C / Inert atmosphere

6.1: lithium hydroxide / tetrahydrofuran; water / 1.5 h / 20 °C / Inert atmosphere

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane; tetrahydrofuran / 6 h / 50 °C / Inert atmosphere

With dmap; hydroxylamine hydrochloride; sodium methylate; boron tribromide; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; zinc; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jm301499r

Reference yield:

5-methoxy-1,3-benzothiazole-2-carbaldehyde oxime (1203605-11-1) → 2-(2-{[5-(2,6-dichloro-phenyl)-[1,2,4]triazin-3-ylamino]-methyl}-benzothiazol-5-yloxy)-N-(2-hydroxy-ethyl)-acetamide (1203603-94-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetic acid; zinc / 3 h / 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 50 - 85 °C / Inert atmosphere

3.1: boron tribromide / dichloromethane / 18 h / -78 - 20 °C / Inert atmosphere

4.1: potassium carbonate / acetone / 0.5 h / 20 °C / Inert atmosphere

4.2: 60 °C / Inert atmosphere

5.1: lithium hydroxide / tetrahydrofuran; water / 1.5 h / 20 °C / Inert atmosphere

6.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane; tetrahydrofuran / 6 h / 50 °C / Inert atmosphere

With dmap; boron tribromide; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; zinc; In tetrahydrofuran; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jm301499r

upstream raw materials:

{[2-({[5-(2,6-dichlorophenyl)-1,2,4-triazin-3-yl]amino}methyl)-1,3-benzothiazol-5-yl]oxy}acetic acid

ethanolamine

5-methoxybenzothiazole-2-carboxaldehyde

5-methoxy-1,3-benzothiazole-2-carbaldehyde oxime

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