N-(6-fluoro-1H-indazol-5-yl)-6-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-pyridine-5-carboxamide

Base Information

• Chemical Name: N-(6-fluoro-1H-indazol-5-yl)-6-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-pyridine-5-carboxamide
• CAS No.: 864082-47-3
• Molecular Formula: C₂₁H₁₆F₄N₄O₂
• Molecular Weight: 432.377
• European Community (EC) Number: 689-442-9
• ChEMBL ID: CHEMBL375312
• DSSTox Substance ID: DTXSID70463946
• Nikkaji Number: J3.573.349C
• Pharos Ligand ID: 529VD5548ZTP
• Wikidata: Q27163215
• Mol file: 864082-47-3.mol

Synonyms:4-(4-(trifluoromethyl)phenyl)-N-(6-fluoro-1H-indazol-5-yl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide;GSK429286

Chemical Property of N-(6-fluoro-1H-indazol-5-yl)-6-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-pyridine-5-carboxamide

Chemical Property:

• Boiling Point: 688.4 °C at 760 mmHg
• PKA: 12.10±0.40(Predicted)
• Flash Point: 370.2 °C
• PSA: 86.88000
• Density: 1.468g/cm³
• LogP: 4.63880
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 432.12093841
• Heavy Atom Count: 31
• Complexity: 748

Purity/Quality:

97% ^*data from raw suppliers

GSK-429286 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC(=O)N1)C2=CC=C(C=C2)C(F)(F)F)C(=O)NC3=C(C=C4C(=C3)C=NN4)F
• Uses: GSK 429286 is a selective Rho-kinase (ROCK) inhibitor.It is orally available and has been shown to dramatically reduce mean arterial pressure in spontaneously hypertensive rats.

Technology Process of N-(6-fluoro-1H-indazol-5-yl)-6-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-pyridine-5-carboxamide

There total 3 articles about N-(6-fluoro-1H-indazol-5-yl)-6-methyl-2-oxo-4-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-pyridine-5-carboxamide 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: 22.0%

4-[4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid (864082-33-7) + 5-amino-6-fluoro-1H-indazole (709046-14-0) → GSK429286 (864082-47-3)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 18h;

Reference yield:

methyl 4-[4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylate (330216-62-1) → GSK429286 (864082-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol

2: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; triethylamine / 4-dimethylaminopyridine / dimethylformamide / 2 h / 80 °C

With sodium hydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dmap; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0609014

Reference yield:

4-Trifluoromethylbenzaldehyde (455-19-6) → GSK429286 (864082-47-3)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; ammonium acetate

2: aq. NaOH / methanol

3: N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; triethylamine / 4-dimethylaminopyridine / dimethylformamide / 2 h / 80 °C

With ammonium acetate; sodium hydroxide; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dmap; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm0609014

upstream raw materials:

4-[4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

5-amino-6-fluoro-1H-indazole

methyl 4-[4-(trifluoromethyl)phenyl]-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylate

4-Trifluoromethylbenzaldehyde