NVP-BAW2881

Base Information

• Chemical Name: NVP-BAW2881
• CAS No.: 861875-60-7
• Molecular Formula: C₂₂H₁₅F₃N₄O₂
• Molecular Weight: 424.382
• Mol file: 861875-60-7.mol

Synonyms:6-(2-amino-pyrimidin-4-yloxy)naphthalene-1-carboxylic acid (3-trifluoromethyl phenyl)amide

Chemical Property of NVP-BAW2881

Chemical Property:

• Solubility.: ≥42.4 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH

Purity/Quality:

99%, ^*data from raw suppliers

6-[(2-amino-4-pyrimidinyl)oxy]-N-[3-(trifluoromethyl)phenyl]-1-naphthalenecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: BAW 2881 is a vascular endothelial growth factor receptor (VEGFR) inhibitor (IC50s = 0.82, 0.037, and 0.42 μM for hVEGFR1, 2, and 3, respectively). It inhibits Tie2 and RET with IC50 values of 0.65 and 0.41 μM, respectively, but demonstrates IC50 values great than 10 μM toward a large panel of additional kinases. BAW 2881 was shown to block VEGF-A-induced proliferation, migration, and tube formation of human umbilical vein endothelial cells and lymphatic endothelial cells in vitro. In a mouse model of psoriasis, both oral and topical administration of BAW 2881 reduced psoriasis-like inflammation in ear skin. Topical application of BAW 2881 also reduced VEGF-A-induced vascular permeability and inhibited contact hypersensitivity reactions and UV-B-induced erythema in the skin of domestic pigs.

Technology Process of NVP-BAW2881

There total 5 articles about NVP-BAW2881 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: 75.0%

6-(2-amino-6-chloro-pyrimidin-4-yloxy)naphthalene-1-carboxylic acid (3-trifluoromethyl phenyl)amide → 6-(2-amino-pyrimidin-4-yloxy)naphthalene-1-carboxylic acid (3-trifluoromethyl phenyl)amide (861875-60-7)

Guidance literature:

With palladium 10% on activated carbon; triethylamine; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b01582

Reference yield:

6-(2-amino-6-chloro-pyrimidin-4-yloxy)naphthalene-1-carboxylic acid (890129-76-7) + 3-trifluoromethylaniline (98-16-8) → 6-(2-amino-pyrimidin-4-yloxy)naphthalene-1-carboxylic acid (3-trifluoromethyl phenyl)amide (861875-60-7)

Guidance literature:

With hydrogen; triethylamine; palladium 10% on activated carbon; In tetrahydrofuran;

Reference yield:

6-hydroxy-1-naphthoic acid (2437-17-4) → 6-(2-amino-pyrimidin-4-yloxy)naphthalene-1-carboxylic acid (3-trifluoromethyl phenyl)amide (861875-60-7)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / acetone / 40 h / 62 °C / Inert atmosphere

2: 4-methyl-morpholine; diethyl cyanophosphonate / N,N-dimethyl-formamide / 20 h / 21 °C / Inert atmosphere

3: palladium 10% on activated carbon; triethylamine / tetrahydrofuran / Inert atmosphere

With 4-methyl-morpholine; diethyl cyanophosphonate; palladium 10% on activated carbon; triethylamine; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.jmedchem.5b01582

upstream raw materials:

6-(2-amino-6-chloro-pyrimidin-4-yloxy)naphthalene-1-carboxylic acid

3-trifluoromethylaniline

6-hydroxy-1-naphthoic acid

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