AZ191

Base Information

• Chemical Name: AZ191
• CAS No.: 1594092-37-1
• Molecular Formula: C24H27N7O
• Molecular Weight: 429.52
• Mol file: 1594092-37-1.mol

Synonyms:AZ191;N-[2-methoxy-4-(4-methyl-1-piperazinyl)phenyl]-4-(1-methyl-1h-pyrrolo[2,3-c]pyridin-3-yl)-2-pyrimidinamine, AZ191;[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-[4-(1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-pyrimidin-2-yl]-amine

Chemical Property of AZ191

Chemical Property:

• Boiling Point: 705.3±70.0 °C(Predicted)
• PKA: 7.76±0.42(Predicted)
• PSA: 71.34000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 3.61020
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble10mg/mL, clear

Purity/Quality:

99%, ^*data from raw suppliers

AZ191 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: AZ191 is a potent and selective DYRK1B inhibitor (1).

Technology Process of AZ191

There total 7 articles about AZ191 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: 23.0%

2-methoxy-4-(4-methylpiperazin-1-yl)aniline (122833-04-9) + 3-(2-chloropyrimidin-4-yl)-1-methyl-1H-pyrrolo[2,3-c]pyridine → N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)-4-(1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-amine (1594092-37-1)

Guidance literature:

With toluene-4-sulfonic acid; In 1-methyl-pyrrolidin-2-one; at 200 ℃; for 2h; Microwave irradiation; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b00098

Reference yield:

6-azaindole (271-29-4) → N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)-4-(1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-amine (1594092-37-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: bromine; sodium hydrogencarbonate / methanol / 3 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane; water / 1 h / 0 °C / Inert atmosphere

3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 18 h / 80 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,4-dioxane / 1 h / 80 °C / Inert atmosphere

5.1: sodium carbonate / water; 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

6.2: 20 h / 20 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / 1-methyl-pyrrolidin-2-one / 2 h / 200 °C / Microwave irradiation; Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; potassium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; sodium hydrogencarbonate; sodium carbonate; toluene-4-sulfonic acid; sodium hydroxide; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.5b00098

Reference yield:

3-bromo-1H-pyrrolo[2,3-c]pyridine (67058-76-8) → N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)-4-(1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-amine (1594092-37-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane; water / 1 h / 0 °C / Inert atmosphere

2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,2-dimethoxyethane / 18 h / 80 °C / Inert atmosphere

3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,4-dioxane / 1 h / 80 °C / Inert atmosphere

4.1: sodium carbonate / water; 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

5.2: 20 h / 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / 1-methyl-pyrrolidin-2-one / 2 h / 200 °C / Microwave irradiation; Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; sodium hydroxide; In 1,4-dioxane; 1-methyl-pyrrolidin-2-one; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.5b00098

upstream raw materials:

6-azaindole

3-bromo-1H-pyrrolo[2,3-c]pyridine

3-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine

2-methoxy-4-(4-methylpiperazin-1-yl)aniline

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