LDN-193189 HCl

Base Information

• Chemical Name: LDN-193189 HCl
• CAS No.: 1062368-62-0
• Molecular Formula: C25H23ClN6
• Molecular Weight: 442.951
• Mol file: 1062368-62-0.mol

Synonyms:4-(6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline hydrochloride;4-(6-(4-(Piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyriMidin-3-yl)quinoline HCl;LDN193189 (Hydrochloride)

Chemical Property of LDN-193189 HCl

Chemical Property:

• PSA: 58.35000
• LogP: 5.21690
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Methanol (Slightly), DMSO (Very Slightly, Heated)

Purity/Quality:

99%+, ^*data from raw suppliers

LDN193189 hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: LDN-193189 HCl 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. 4-(6-(4-(Piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline Hydrochoride is a selective inhibitor of bone morphogenetic protein (BMP) pathway, useful in the treatment of diseases.

Technology Process of LDN-193189 HCl

There total 4 articles about LDN-193189 HCl 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: 98.0%

C30H30N6O2 (1062368-27-7) → 4-(6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline hydrochloride (1062368-62-0,2310134-98-4,1435934-00-1)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; water; at 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2008.06.052

Reference yield:

6-bromo-pyrazolo[1,5-α]pyrimidine (705263-10-1) → 4-(6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline hydrochloride (1062368-62-0,2310134-98-4,1435934-00-1)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 5 h / 110 °C / Inert atmosphere

2: N-Bromosuccinimide / dichloromethane / 0 °C

3: potassium phosphate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / butan-1-ol / 0.25 h / 150 °C / Inert atmosphere; Microwave irradiation

4: hydrogenchloride / 1,4-dioxane / 24 h / 20 °C

With hydrogenchloride; potassium phosphate; N-Bromosuccinimide; potassium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrakis(triphenylphosphine) palladium⁽⁰⁾; XPhos; In 1,4-dioxane; dichloromethane; butan-1-ol;

Reference yield:

tert-butyl 4-(4-(3-bromopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)piperazine-1-carboxylate (1062368-26-6) → 4-(6-(4-(piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline hydrochloride (1062368-62-0,2310134-98-4,1435934-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / butan-1-ol / 0.25 h / 150 °C / Inert atmosphere; Microwave irradiation

2: hydrogenchloride / 1,4-dioxane / 24 h / 20 °C

With hydrogenchloride; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In 1,4-dioxane; butan-1-ol;

upstream raw materials:

C₃₀H₃₀N₆O₂

6-bromo-pyrazolo[1,5-α]pyrimidine

C₂₁H₂₅N₅O₂

tert-butyl 4-(4-(3-bromopyrazolo[1,5-a]pyrimidin-6-yl)phenyl)piperazine-1-carboxylate

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.