5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a]

Base Information

• Chemical Name: 5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a]
• CAS No.: 1062368-49-3
• Molecular Formula: C22H16N4O
• Molecular Weight: 352.395
• Hs Code.: 29339900
• Mol file: 1062368-49-3.mol

Synonyms:5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a];ML-347(LDN-193719);5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline;LDN 193719;Quinoline, 5-[6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]-;5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline ML-347(LDN-193719);LDN 193719 5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline;ML347(DN193719)

Chemical Property of 5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a]

Chemical Property:

• Melting Point: 209-210℃
• PSA: 52.31000
• LogP: 4.62010
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥5.87 mg/mL in DMSO with gentle warming

Purity/Quality:

98% ^*data from raw suppliers

ML 347 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: LDN 193719 is a selective bone morphogenetic protein receptor (BMP) inhibitor for ALK2.

Technology Process of 5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a]

There total 6 articles about 5-[6-(4-Methoxyphenyl)pyrazolo[1,5-a] 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: 76.0%

5-bromoquinoline (4964-71-0) + C13H11N3O (1062368-61-9) → ML347 (1062368-49-3)

Guidance literature:

With potassium acetate; cesium acetate; palladium diacetate; In N,N-dimethyl acetamide; at 150 ℃; for 4h; Inert atmosphere;

Reference yield: 70.0%

3-(bromo)-6-(4-methoxyphenyl)-pyrazolo(1,5-A)pyrimidine (216661-83-5) + quinolin-5-ylboronic acid (355386-94-6) → ML347 (1062368-49-3)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In butan-1-ol; at 150 ℃; for 0.25h; Microwave irradiation;

DOI:10.1016/j.bmcl.2008.06.052

Reference yield: 47.0%

3-iodo-6-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine (709631-61-8) + quinolin-5-ylboronic acid (355386-94-6) → ML347 (1062368-49-3)

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:

3-(bromo)-6-(4-methoxyphenyl)-pyrazolo(1,5-A)pyrimidine

quinolin-5-ylboronic acid

C₁₃H₁₁N₃O

2-(4-methoxyphenyl)malondialdehyde

Refernces

• 1、 Engers, Darren W.,Frist, Audrey Y.,Lindsley, Craig W.,Hong, Charles C.,Hopkins, Corey R.. "Synthesis and structure-activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of Dorsomorphin: The discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe". . p. 3248 - 3252. Retrieved 2013/06/27.