3-(5-{4-[5-(tert-butoxycarbonylaminomethyl)pyridin-3-yl]thieno[3,2-d]pyrimidin-6-yl}-2-methoxypyridin-3-ylsulfamoyl)benzoic acid

Base Information

• Chemical Name: 3-(5-{4-[5-(tert-butoxycarbonylaminomethyl)pyridin-3-yl]thieno[3,2-d]pyrimidin-6-yl}-2-methoxypyridin-3-ylsulfamoyl)benzoic acid
• CAS No.: 1414467-02-9
• Molecular Formula: C₃₀H₂₈N₆O₇S₂
• Molecular Weight: 648.72
• Mol file: 1414467-02-9.mol

Synonyms:3-(5-{4-[5-(tert-butoxycarbonylaminomethyl)pyridin-3-yl]thieno[3,2-d]pyrimidin-6-yl}-2-methoxypyridin-3-ylsulfamoyl)benzoic acid

Chemical Property of 3-(5-{4-[5-(tert-butoxycarbonylaminomethyl)pyridin-3-yl]thieno[3,2-d]pyrimidin-6-yl}-2-methoxypyridin-3-ylsulfamoyl)benzoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(5-{4-[5-(tert-butoxycarbonylaminomethyl)pyridin-3-yl]thieno[3,2-d]pyrimidin-6-yl}-2-methoxypyridin-3-ylsulfamoyl)benzoic acid

There total 4 articles about 3-(5-{4-[5-(tert-butoxycarbonylaminomethyl)pyridin-3-yl]thieno[3,2-d]pyrimidin-6-yl}-2-methoxypyridin-3-ylsulfamoyl)benzoic acid 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: 37.0%

{5-[6-(5-amino-6-methoxypyridin-3-yl)thieno[3,2-d]pyrimidin-4-yl]pyridin-3-ylmethyl}carbamic acid tert-butyl ester (1414466-96-8) + 3-Carboxybenzenesulfonyl chloride (4025-64-3) → 3-(5-{4-[5-(tert-butoxycarbonylaminomethyl)pyridin-3-yl]thieno[3,2-d]pyrimidin-6-yl}-2-methoxypyridin-3-ylsulfamoyl)benzoic acid (1414467-02-9)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 3.5h;

DOI:10.1021/acsmedchemlett.1c00412

Reference yield:

4-chlorothieno[3,2-d]pyrimidine (16269-66-2) → 3-(5-{4-[5-(tert-butoxycarbonylaminomethyl)pyridin-3-yl]thieno[3,2-d]pyrimidin-6-yl}-2-methoxypyridin-3-ylsulfamoyl)benzoic acid (1414467-02-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C

1.2: 2 h / -50 °C

2.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,4-dioxane / 2 h / 120 °C / Sealed tube

3.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Sealed tube

4.1: pyridine / 3.5 h / 0 - 20 °C

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; water; 2.1: |Suzuki Coupling / 3.1: |Suzuki Coupling;

DOI:10.1021/acsmedchemlett.1c00412

Reference yield:

5-(4-chlorothieno[3,2-d]pyrimidin-6-yl)-2-methoxypyridin-3-ylamine (1414466-90-2) → 3-(5-{4-[5-(tert-butoxycarbonylaminomethyl)pyridin-3-yl]thieno[3,2-d]pyrimidin-6-yl}-2-methoxypyridin-3-ylsulfamoyl)benzoic acid (1414467-02-9)

Guidance literature:

Multi-step reaction with 2 steps

1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,4-dioxane / 3 h / 100 °C / Sealed tube

2: pyridine / 3.5 h / 0 - 20 °C

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; 1: |Suzuki Coupling;

DOI:10.1021/acsmedchemlett.1c00412

upstream raw materials:

4-chlorothieno[3,2-d]pyrimidine

{5-[6-(5-amino-6-methoxypyridin-3-yl)thieno[3,2-d]pyrimidin-4-yl]pyridin-3-ylmethyl}carbamic acid tert-butyl ester

3-Carboxybenzenesulfonyl chloride

5-(4-chlorothieno[3,2-d]pyrimidin-6-yl)-2-methoxypyridin-3-ylamine

Downstream raw materials:

C₂₄H₁₈N₆O₅S₂