6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

Base Information

• Chemical Name: 6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine
• CAS No.: 1062368-24-4
• Molecular Formula: C25H22N6
• Molecular Weight: 406.49
• Hs Code.: 29339900
• Mol file: 1062368-24-4.mol

Synonyms:Quinoline, 4-[6-[4-(1-piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-;LDN 193189;

Chemical Property of 6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

Chemical Property:

• PKA: 8.79±0.10(Predicted)
• PSA: 58.35000
• Density: 1.337 g/cm³
• LogP: 4.41490
• Storage Temp.: ?20°C
• Solubility.: H2O: soluble5mg/mL, clear (warmed)

Purity/Quality:

99% ^*data from raw suppliers

LDN193189 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Normal development and tissue repair are controlled in part by SMADs, a family of intracellular proteins that are activated by signaling via serine/threonine kinase receptors of the TGF-β superfamily. LDN-193189 inhibits SMAD1/5/8 phosphorylation by the bone morphogenetic protein (BMP) type I receptors, which are known as activin receptor-like kinases (ALKs), with an IC50 value of 4.9 nM. In in vitro kinase assays, it shows specificity for ALK1, 2, 3, and 6 (IC50s = 0.8, 0.8, 5.3, and 16.7 nM, respectively) over ALK4 and 5 (IC50s = 101 and 350 nM, respectively). LDN-193189 has been used to inhibit BMP type I receptor activity to study the pathogenesis of fibrodysplasia ossificans progressive, a congenital hyperossification disorder, and to examine the role of osteogenesis in prostate tumor metastases in bone.
• Uses: 4-(6-(4-(Piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline, is a selective inhibitor of bone morphogenetic protein (BMP) pathway, useful in the treatment of diseases. Potent BMP Inhibitor?, Promotes hPSC Neural Induction?.

Technology Process of 6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

There total 8 articles about 6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine 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: 86.0%

C33H28N6O2 (1062368-23-3) → LDN-193189 (1062368-24-4)

Guidance literature:

With 5% Pd/C; hydrogen; In methanol; dichloromethane; at 20 ℃; for 4h; under 760.051 Torr;

DOI:10.1016/j.bmcl.2008.06.052

Reference yield:

quinoline-4-carboxaldehyde (4363-93-3) → LDN-193189 (1062368-24-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: methanol; sodium tetrahydroborate / 1.33 h / 0 - 20 °C

2.1: thionyl chloride / dichloromethane / 2.33 h / 0 - 20 °C

2.2: pH > 7 / Saturated solution

3.1: N,N-dimethyl-formamide / 20 - 80 °C

4.1: 6 h / 120 °C

5.1: hydrazine monohydrobromide / ethanol; water / 5 h / 110 °C

5.2: Saturated solution

6.1: acetic acid / ethanol / 0.08 h / 170 °C / Microwave irradiation

7.1: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere

8.1: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr

With methanol; sodium tetrahydroborate; thionyl chloride; hydrazine monohydrobromide; potassium tert-butylate; hydrogen; acetic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 5%-palladium/activated carbon; johnphos; In methanol; 1,1-dichloroethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

4-quinolylmethanol (6281-32-9) → LDN-193189 (1062368-24-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: thionyl chloride / dichloromethane / 2.33 h / 0 - 20 °C

1.2: pH > 7 / Saturated solution

2.1: N,N-dimethyl-formamide / 20 - 80 °C

3.1: 6 h / 120 °C

4.1: hydrazine monohydrobromide / ethanol; water / 5 h / 110 °C

4.2: Saturated solution

5.1: acetic acid / ethanol / 0.08 h / 170 °C / Microwave irradiation

6.1: potassium tert-butylate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; johnphos / 1,1-dichloroethane / 20 h / 100 °C / Inert atmosphere

7.1: hydrogen / 5%-palladium/activated carbon / methanol; dichloromethane / 4 h / 20 °C / 760.05 Torr

With thionyl chloride; hydrazine monohydrobromide; potassium tert-butylate; hydrogen; acetic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 5%-palladium/activated carbon; johnphos; In methanol; 1,1-dichloroethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

C₃₃H₂₈N₆O₂

quinoline-4-carboxaldehyde

4-quinolylmethanol

4-(chloromethyl)quinoline

Refernces

• 1、 Cuny, Gregory D.,Yu, Paul B.,Laha, Joydev K.,Xing, Xuechao,Liu, Ji-Feng,Lai, Carol S.,Deng, Donna Y.,Sachidanandan, Chetana,Bloch, Kenneth D.,Peterson, Randall T.. "Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors". supporting information; scheme or table. p. 4388 - 4392. Retrieved 2009/04/06.