2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE

Base Information

• Chemical Name: 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE
• CAS No.: 446859-33-2
• Molecular Formula: C17H13N5
• Molecular Weight: 287.32
• Mol file: 446859-33-2.mol

Synonyms:1,5-Naphthyridine, 2-[3-(6-methyl-2-pyridinyl)-1H-pyrazol-4-yl]-;Alk 5 Inhibitor II;SJN 2511;

Chemical Property of 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 195 °C
• Refractive Index: 1.692
• Boiling Point: 501.911 °C at 760 mmHg
• PKA: 10.05±0.50(Predicted)
• Flash Point: 230.461 °C
• PSA: 67.35000
• Density: 1.297 g/cm³
• LogP: 3.39030
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: >20mg/mL

Purity/Quality:

98%,99%, ^*data from raw suppliers

RepSox ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Description: RepSox (446859-33-2) is a potent (IC50?ALK5 auto-P= 4 nM; IC50?TGF-β cellular assay = 23 nM) inhibitor of the TGF-β type I receptor (ALK5).1?RepSox can replace Sox2 in reprogramming adult cells into pluripotent stem cells via induction of Nanog transcription.2?It was able to convert astrocytes into neuronal cells as part of a small molecule cocktail (along with valproic acid and CHIR99021).3,4
• Uses: Alk 5 Inhibitor II is a selective ATP competitive inhibitor of transforming growth factor-β (TGFβ). A potential drug for the treatment of fibrosis and cancer. RepSox has been used as an inhibitor of autophosphorylation of the transforming growth factor β type I receptor kinase (ALK5). It has also been used as a basal media component for culturing human Pluripotent stem cells.

Technology Process of 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE

There total 4 articles about 2-(3-(6-METHYLPYRIDIN-2-YL)-1H-PYRAZOL-4-YL)-1,5-NAPHTHYRIDINE 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: 72.0%

1-(6-methylpyridin-2-yl)-2-(1,5-naphthyridin-2-yl)ethan-1-one (446297-56-9) → repsox (446859-33-2)

Guidance literature:

1-(6-methylpyridin-2-yl)-2-(1,5-naphthyridin-2-yl)ethan-1-one; With acetic acid; N,N-dimethyl-formamide dimethyl acetal; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

With hydrazine hydrate; In N,N-dimethyl-formamide; at 50 ℃; for 2h;

DOI:10.1016/j.bmc.2010.04.071

Reference yield: 30.6%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + 1-(6-methylpyridin-2-yl)-2-(1,5-naphthyridin-2-yl)ethan-1-one (446297-56-9) → repsox (446859-33-2)

Guidance literature:

N,N-dimethyl-formamide dimethyl acetal; 1-(6-methylpyridin-2-yl)-2-(1,5-naphthyridin-2-yl)ethan-1-one; With acetic acid; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

With hydrazine hydrate; In N,N-dimethyl-formamide; at 50 ℃; for 2h;

DOI:10.1021/jm0400247

Reference yield:

5-Amino-2-methylpyridine (80287-53-2,3430-14-6) → repsox (446859-33-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 55 percent / aq. sodium m-nitrobenzenesulfonate; sulfuric acid; boric acid / iron sulfate heptahydrate / 18 h / 135 °C

2.1: 76 percent / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 21 h / -78 - 20 °C

3.1: acetic acid / dimethylformamide / 1 h / 20 °C

3.2: 30.6 percent / hydrazine monohydrate / dimethylformamide / 2 h / 50 °C

With sulfuric acid; boric acid; potassium hexamethylsilazane; acetic acid; sodium 3-nitrobenzenesulfonate; iron(II) sulfate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1.1: Skraup reaction;

DOI:10.1021/jm0400247

upstream raw materials:

N,N-dimethyl-formamide dimethyl acetal

1-(6-methylpyridin-2-yl)-2-(1,5-naphthyridin-2-yl)ethan-1-one

5-Amino-2-methylpyridine

2-methyl-[1,5]naphthyridine

Refernces

• 1、 Gellibert, Fran?oise,Woolven, James,Fouchet, Marie-Hélène,Mathews, Neil,Goodland, Helen,Lovegrove, Victoria,Laroze, Alain,Nguyen, Van-Loc,Sautet, Stéphane,Wang, Ruolan,Janson, Cheryl,Smith, Ward,Krysa, Ga?l,Boullay, Valérie,De Gouville, Anne-Charlotte,Huet, Stéphane,Hartley, David. "Identification of 1,5-naphthyridine derivatives as a novel series of potent and selective TGF-β type I receptor inhibitors". . p. 4494 - 4506. Retrieved 2007/10/03.