LDN212854

Base Information

• Chemical Name: LDN212854
• CAS No.: 1432597-26-6
• Molecular Formula: C25H22N6
• Molecular Weight: 406.49
• Mol file: 1432597-26-6.mol

Synonyms:LDN212854;5-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyriMidin-3-yl]quinoline;Quinoline, 5-[6-[4-(1-piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-;BMP Inhibitor III;5-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline LDN 212854;LDN 212854 5-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline;LDN-212854, >=98%

Chemical Property of LDN212854

Chemical Property:

• PKA: 8.79±0.10(Predicted)
• PSA: 58.35000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 4.41490
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble1mg/mL, clear (warmed)

Purity/Quality:

98% ^*data from raw suppliers

5-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Description: LDN-212854 is a potent and selective BMP receptor inhibitor with IC50 of 1.3 nM for ALK2, about 2-, 66-, 1641-, and 7135-fold selectivity over ALK1, ALK3, ALK4, and ALK5, respectively.
• Uses: 5-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline, contains the pyrazolo[1,5-a]pyrimidine scaffold, acting as a novel and selective bone morphogenetic protein receptor (BMP) inhibitors. It is a COVID19-related research product.

Technology Process of LDN212854

There total 5 articles about LDN212854 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: 94.0%

C30H30N6O2 → 5-[6-[4-(1-piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline (1432597-26-6)

Guidance literature:

With hydrogenchloride; In methanol; water; for 1h; Reflux;

Reference yield:

6-bromo-pyrazolo[1,5-α]pyrimidine (705263-10-1) → 5-[6-[4-(1-piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline (1432597-26-6)

Guidance literature:

Multi-step reaction with 3 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / 1,4-dioxane; water / 0.5 h / 150 °C / Inert atmosphere; Microwave irradiation

2: N-iodo-succinimide / N,N-dimethyl-formamide / 40 h / 20 °C

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / 1,4-dioxane; water / 0.5 h / 120 °C / Inert atmosphere; Microwave irradiation

With potassium phosphate; N-iodo-succinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; water; N,N-dimethyl-formamide; 1: |Suzuki-Miyaura Coupling / 3: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.bmcl.2013.03.113

Reference yield:

C16H16IN5 (1435615-10-3) + quinolin-5-ylboronic acid (355386-94-6) → 5-[6-[4-(1-piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline (1432597-26-6)

Guidance literature:

With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; water; at 120 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.bmcl.2013.03.113

upstream raw materials:

C₁₆H₁₆IN₅

quinolin-5-ylboronic acid

C₁₆H₁₇N₅

6-bromo-pyrazolo[1,5-α]pyrimidine

Refernces

• 1、 -. "BMP INHIBITORS AND METHODS OF USE THEREOF". . . Retrieved 2014/09/29.