AZD5153

Base Information

• Chemical Name: AZD5153
• CAS No.: 1869912-40-2
• Molecular Formula: C₁₁H₈O₃*C₂₅H₃₃N₇O₃
• Molecular Weight: 667.765

Synonyms:

Chemical Property of AZD5153

Chemical Property:

Purity/Quality:

99%, ^*data from raw suppliers

AZD5153(6-?Hydroxy-?2-?naphthoicAcid) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: AZD5153 (6-?Hydroxy-?2-?naphthoic Acid) is a potent triazolopyridazine-based Bromodomain (BRD4) and Extraterminal (BET) inhibitor used in cancer treatments.

Technology Process of AZD5153

There total 9 articles about AZD5153 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:

6-Hydroxy-2-naphthoic acid (16712-64-4) + (3R)?4-[2-[4-[1-(3-methoxy-[1,2,4]triazolo[4,3?b]pyridazin-6-yl)-4-piperidyl]phenoxy]ethyl]-1,3-dimethyl-piperazin-2-one (1869912-39-9) → (R)-4-(2-(4-(1-(3-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl)phenoxy)ethyl)-1,3-dimethylpiperazin-2-one: 6-hydroxy-2-naphthoic acid(1:1) co-crystal (1869912-40-2)

Guidance literature:

In methanol; at 20 ℃;

Reference yield:

benzyl 1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylate (286961-24-8) → (R)-4-(2-(4-(1-(3-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl)phenoxy)ethyl)-1,3-dimethylpiperazin-2-one: 6-hydroxy-2-naphthoic acid(1:1) co-crystal (1869912-40-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium carbonate; (p-hydroxyphenyl)boronic acid / 1,4-dioxane; water / 0.17 h / Inert atmosphere

1.2: 1 h / 80 °C

2.1: 5%-palladium/activated carbon; hydrogen / methanol / 2 h / 25 °C / 3750.38 Torr

3.1: hydrogen bromide / tetrahydrofuran; water / 0.5 h

4.1: N-ethyl-N,N-diisopropylamine / ethanol / 18 h / 55 °C

5.1: tributylphosphine; 1,1'-(Azodicarbonyl)dipiperidin / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere

6.1: methanol / 20 °C

With tributylphosphine; 5%-palladium/activated carbon; 1,1'-(Azodicarbonyl)dipiperidin; (p-hydroxyphenyl)boronic acid; hydrogen bromide; hydrogen; sodium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water;

Reference yield:

benzyl 4-(4-hydroxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (1166820-03-6) → (R)-4-(2-(4-(1-(3-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl)phenoxy)ethyl)-1,3-dimethylpiperazin-2-one: 6-hydroxy-2-naphthoic acid(1:1) co-crystal (1869912-40-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 5%-palladium/activated carbon; hydrogen / methanol / 2 h / 25 °C / 3750.38 Torr

2: hydrogen bromide / tetrahydrofuran; water / 0.5 h

3: N-ethyl-N,N-diisopropylamine / ethanol / 18 h / 55 °C

4: tributylphosphine; 1,1'-(Azodicarbonyl)dipiperidin / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere

5: methanol / 20 °C

With tributylphosphine; 5%-palladium/activated carbon; 1,1'-(Azodicarbonyl)dipiperidin; hydrogen bromide; hydrogen; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

upstream raw materials:

benzyl 1,2,3,6-tetrahydro-4-(trifluoromethylsulphonyloxy)-pyridine-1-carboxylate

benzyl 4-(4-hydroxyphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

4-(4-hydroxyphenyl)-1,2,3,6-tetrahydropiperidine

4-(piperidine-4-yl)phenol hydrobromide

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