4′-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)biphenyl-2-ol

Base Information

• Chemical Name: 4′-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)biphenyl-2-ol
• CAS No.: 1563175-44-9
• Molecular Formula: C₂₈H₃₇N₅OS
• Molecular Weight: 491.701

Synonyms:4′-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)biphenyl-2-ol

Chemical Property of 4′-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)biphenyl-2-ol

Chemical Property:

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Technology Process of 4′-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)biphenyl-2-ol

There total 9 articles about 4′-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)biphenyl-2-ol 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: 55.0%

N6-(2-(4-(2′-methoxybiphenyl-4-yl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine (1563175-38-1) → 4′-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)biphenyl-2-ol (1563175-44-9)

Guidance literature:

With boron tribromide; In dichloromethane; at -78 - 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/jm401883v

Reference yield:

1-(2′-methoxy-biphenyl-4-yl)piperazine (1226381-81-2) → 4′-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)biphenyl-2-ol (1563175-44-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / acetonitrile / 14 h / Inert atmosphere; Reflux

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

3.2: 1.33 h / 20 °C / Inert atmosphere

4.1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C / Inert atmosphere

5.1: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; tetrabutyl ammonium fluoride; boron tribromide; sodium tris(acetoxy)borohydride; potassium carbonate; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; acetonitrile; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;

DOI:10.1021/jm401883v

Reference yield:

1-(2-(t-butyldimethylsilyloxy)ethyl)-4-(2′-methoxybiphenyl-4-yl)piperazine (1563175-21-2) → 4′-(4-(2-((2-amino-4,5,6,7-tetrahydrobenzo[d]thiazol-6-yl)(propyl)amino)ethyl)piperazin-1-yl)biphenyl-2-ol (1563175-44-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

2.2: 1.33 h / 20 °C / Inert atmosphere

3.1: sodium tris(acetoxy)borohydride / dichloromethane / 48 h / 20 °C / Inert atmosphere

4.1: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; tetrabutyl ammonium fluoride; boron tribromide; sodium tris(acetoxy)borohydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1021/jm401883v

upstream raw materials:

1-(2′-methoxy-biphenyl-4-yl)piperazine

1-(2-(t-butyldimethylsilyloxy)ethyl)-4-(2′-methoxybiphenyl-4-yl)piperazine

tert-butyl 4-(4-iodophenyl)tetrahydro-1(2H)-pyrazinecarboxylate

2-(4-(2′-methoxybiphenyl-4-yl)piperazin-1-yl)ethanol

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