n-Methyl-2-[[3-[(1e)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2h-pyran-2-yl)-1h-indazol-6-yl]thio]benzamide

Base Information

• Chemical Name: n-Methyl-2-[[3-[(1e)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2h-pyran-2-yl)-1h-indazol-6-yl]thio]benzamide
• CAS No.: 885126-35-2
• Molecular Formula: C₂₇H₂₆N₄O₂S
• Molecular Weight: 470.595
• European Community (EC) Number: 886-852-1
• DSSTox Substance ID: DTXSID801111480
• Mol file: 885126-35-2.mol

Synonyms:885126-35-2;n-methyl-2-[[3-[(1e)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2h-pyran-2-yl)-1h-indazol-6-yl]thio]benzamide;N-methyl-2-[1-(oxan-2-yl)-3-[(E)-2-pyridin-2-ylethenyl]indazol-6-yl]sulfanylbenzamide;(E)-N-methyl-2-(3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ylthio)benzamide;Axitinib Tetrahydro-2H-pyran;SCHEMBL13446211;SCHEMBL18186761;DTXSID801111480;AKOS025401878;AC-26795;DB-353554

Chemical Property of n-Methyl-2-[[3-[(1e)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2h-pyran-2-yl)-1h-indazol-6-yl]thio]benzamide

Chemical Property:

• Boiling Point: 714.2 °C at 760 mmHg
• Flash Point: 385.8 °C
• PSA: 97.83000
• Density: 1.28 g/cm³
• LogP: 6.38640
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 470.17764726
• Heavy Atom Count: 34
• Complexity: 706

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC(=O)C1=CC=CC=C1SC2=CC3=C(C=C2)C(=NN3C4CCCCO4)C=CC5=CC=CC=N5
• Isomeric SMILES: CNC(=O)C1=CC=CC=C1SC2=CC3=C(C=C2)C(=NN3C4CCCCO4)/C=C/C5=CC=CC=N5
• Uses: Axitinib Tetrahydro-2H-pyran is an intermediate in the synthesis of Axitinib (A794650). The Tetrahydro-2H-pyran moiety acts as a protecting group.

Technology Process of n-Methyl-2-[[3-[(1e)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2h-pyran-2-yl)-1h-indazol-6-yl]thio]benzamide

There total 20 articles about n-Methyl-2-[[3-[(1e)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2h-pyran-2-yl)-1h-indazol-6-yl]thio]benzamide 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: 87.2%

(Ε)-6-iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole + N-methyl-2-sulfanylbenzamide (20054-45-9) → (E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide (885126-35-2)

Guidance literature:

N-methyl-2-sulfanylbenzamide; With potassium hydroxide; In N,N-dimethyl-formamide; at 60 ℃; for 1h; Inert atmosphere;

With copper(l) iodide; 1,2-diamino-benzene; In N,N-dimethyl-formamide; at 60 ℃; for 1h; Inert atmosphere;

(Ε)-6-iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole; In N,N-dimethyl-formamide; at 60 - 120 ℃; Temperature; Inert atmosphere;

Reference yield: 70.0%

3,4-dihydro-2H-pyran (110-87-2) + axitinib (319460-85-0,885126-40-9) → (E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide (885126-35-2)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 80 ℃; for 16h;

Reference yield: 62.0%

N-methyl-2-sulfanylbenzamide (20054-45-9) + (E)-6-bromo-3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole → (E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide (885126-35-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In neat (no solvent); for 0.833333h; chemoselective reaction; Milling;

DOI:10.3762/bjoc.14.66

upstream raw materials:

2-vinylpyridine

N-1 THP-protected 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide

N-methyl-2-sulfanylbenzamide

(Ε)-6-nitro-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole