N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)acetamide

Base Information

• Chemical Name: N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)acetamide
• CAS No.: 446289-32-3
• Molecular Formula: C₂₆H₂₄N₆O₅S
• Molecular Weight: 532.58
• Mol file: 446289-32-3.mol

Synonyms:N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)acetamide

Chemical Property of N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)acetamide

There total 9 articles about N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)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:

5-bromo-2-chloro-3-nitropyridine (67443-38-3) → N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)acetamide (446289-32-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 1.5 h / -78 - -40 °C

2.1: sodium methylate; copper(I) bromide / 16 h / 110 - 120 °C / Sealed tube

3.1: aluminum (III) chloride / dichloromethane / 0.17 h / 20 °C

3.2: 8 h / 20 °C

4.1: potassium carbonate / methanol; water / 8 h / 20 °C

5.1: 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8 h / 20 °C

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 10 h / 110 - 120 °C / Sealed tube

With aluminum (III) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; copper(I) bromide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 3.1: |Friedel-Crafts Acylation / 3.2: |Friedel-Crafts Acylation;

DOI:10.1021/acs.jmedchem.8b00759

Reference yield:

1-(4-benzoylpiperazin-1-yl)-2-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione (446285-02-5) + N-(5-(tributylstannyl)thiazol-2-yl)acetamide (446286-45-9) → N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)acetamide (446289-32-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 110 - 120 ℃; for 10h; Sealed tube;

DOI:10.1021/acs.jmedchem.8b00759

Reference yield:

potassium 2-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (446284-78-2) → N-(5-(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)thiazol-2-yl)acetamide (446289-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 8 h / 20 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 10 h / 110 - 120 °C / Sealed tube

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.8b00759

upstream raw materials:

potassium 2-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate

5-bromo-2-chloro-3-nitropyridine

1-(4-benzoylpiperazin-1-yl)-2-(7-chloro-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)ethane-1,2-dione

N-(5-(tributylstannyl)thiazol-2-yl)acetamide

Downstream raw materials:

1-(7-(2-aminothiazol-5-yl)-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-benzoylpiperazin-1-yl)ethane-1,2-dione