N-[3-[(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-1-propanesulfonamide

Base Information

• Chemical Name: N-[3-[(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-1-propanesulfonamide
• CAS No.: 918505-84-7
• Molecular Formula: C₁₇H₁₄ClF₂N₃O₃S
• Molecular Weight: 413.832
• Mol file: 918505-84-7.mol

Synonyms:N-(3-(5-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide;N-[3-[(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-1-propanesulfonamide;

Chemical Property of N-[3-[(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-1-propanesulfonamide

Chemical Property:

• Refractive Index: 1.645
• PKA: 6.20±0.10(Predicted)
• PSA: 100.30000
• Density: 1.549 g/cm³
• LogP: 5.03100
• Storage Temp.: +2C to +8C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

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

PLX4720 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: The Raf kinases activate cellular pathways that lead to cell proliferation and can contribute to certain types of cancer. Mutations in the kinase B-Raf are involved in a wide range of cancers. In particular, the mutation B-RafV600E occurs in melanomas and thyroid cancer but is poorly targeted by many inhibitors of wild type B-Raf. PLX4720 is an orally-available, highly selective inhibitor of B-RafV600E (IC50 = 13 nM). It is less effective against wild type B-Raf (IC50 = 160 nM) as well as several other kinases. PLX4720 induces cell cycle arrest and apoptosis in cells and xenografts expressing the mutant of B-Raf.
• Uses: PLX4720 is a selective inhibitor of mutant B-RAF and its analog, PLX4032, is currently undergoing clinical trials in melanoma. Labelled PLX4720. It is a selective inhibitor of mutant B-RAF and its analog, PLX4032, is currently undergoing clinical trials in melanoma. A potent and selective inhibitor of B-RafV600E and c-Raf-1Y340D/Y341D with IC50s of 13 nM and 6.7 nM, respectively.

Technology Process of N-[3-[(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-1-propanesulfonamide

There total 4 articles about N-[3-[(5-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-1-propanesulfonamide 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: 87.0%

N-(3-((5-chloro-1H-pyrrolo[2,3-b]pyridine-3-yl)(hydroxyl)methyl)2,4-difluorophenyl)propane-1-sulfonamide (1021854-28-3) → N-(3-(5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonoamide (918505-84-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; water; at 100 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1016/j.tetlet.2012.05.137

Reference yield:

N-(3,5-difluorophenyl)propane-1-sulfonamide (918523-57-6) → N-(3-(5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonoamide (918505-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 0 °C / Inert atmosphere

1.2: 1.5 h / -78 - 110 °C / Microwave irradiation

2.1: potassium carbonate / methanol; water / 0.5 h / 130 °C / Microwave irradiation

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane; water / 0.17 h / 100 °C / Microwave irradiation

With potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1016/j.tetlet.2012.05.137

Reference yield:

2,4-difluorophenylamine (367-25-9,76563-56-9) → N-(3-(5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonoamide (918505-84-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine; dmap / dichloromethane / 0.5 h / 100 °C / Microwave irradiation

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 0 °C / Inert atmosphere

2.2: 1.5 h / -78 - 110 °C / Microwave irradiation

3.1: potassium carbonate / methanol; water / 0.5 h / 130 °C / Microwave irradiation

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane; water / 0.17 h / 100 °C / Microwave irradiation

With pyridine; dmap; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1016/j.tetlet.2012.05.137

upstream raw materials:

N-(3-((5-chloro-1H-pyrrolo[2,3-b]pyridine-3-yl)(hydroxyl)methyl)2,4-difluorophenyl)propane-1-sulfonamide

N-(3,5-difluorophenyl)propane-1-sulfonamide

2,4-difluorophenylamine

Refernces

• 1、 -. "PYRROLO[2,3-B] PYRIDINE DERIVATIVES AS PROTEIN KINASE INHIBITORS". Page/Page column 93. . Retrieved 2010/11/25.