2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid

Base Information

• Chemical Name: 2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid
• CAS No.: 1476064-49-9
• Molecular Formula: C₄₄H₅₇N₅O₆
• Molecular Weight: 751.966
• Mol file: 1476064-49-9.mol

Synonyms:2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid

Chemical Property of 2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid

There total 5 articles about 2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid 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: 83.0%

2-({[5-(2,6-dimethoxyphenyl)-1-(2-isopropyl-4-{[methyl(3-{methyl[6-(triisopropylsilyl)hex-5-yn-1-yl]amino}propyl)amino]carbonyl}phenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid (1476064-44-4) → 2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid (1476064-49-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/jm401491e

Reference yield:

2-({[1-(4-bromo-2-isopropylphenyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid (1476064-46-6) + C11H22N2 + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → 2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid (1476064-49-9)

Guidance literature:

2-({[1-(4-bromo-2-isopropylphenyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid; C₁₁H₂₂N₂; molybdenum hexacarbonyl; With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; at 140 ℃; for 0.5h; Microwave irradiation;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/acschembio.5b00965

Reference yield:

(6-chlorohex-1-yn-1-yl)triisopropylsilane → 2-({[5-(2,6-dimethoxyphenyl)-1-(4-{[{3-[hex-5-yn-1-yl(methyl)amino]propyl}(methyl)amino]carbonyl}-2-isopropylphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid (1476064-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium iodide; potassium carbonate / acetonitrile / 71 h / Reflux

2: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tri tert-butylphosphoniumtetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene / 1,4-dioxane / 0.5 h / 140 °C / Inert atmosphere; Microwave irradiation

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tetrabutyl ammonium fluoride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; 1,4-dioxane; acetonitrile;

DOI:10.1021/jm401491e

upstream raw materials:

1-chloro-5-hexyne

N,N'-dimethyl-N-[6-(triisopropylsilyl)hex-5-ynyl]propane-1,3-diamine

2-({[5-(2,6-dimethoxyphenyl)-1-(2-isopropyl-4-{[methyl(3-{methyl[6-(triisopropylsilyl)hex-5-yn-1-yl]amino}propyl)amino]carbonyl}phenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid

2-({[1-(4-bromo-2-isopropylphenyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid

Downstream raw materials:

2-[({5-(2,6-dimethoxyphenyl)-1-[4-({[3-({4-[1-(2-deoxy-2-fluoro-β-D-glucopyranosyl)-1H-1,2,3-triazole-4-yl]butyl}(methyl)amino)propyl](methyl)amino}carbonyl)-2-isopropylphenyl]-1Hpyrazole-3-yl}carbonyl)amino]adamantane-2-carboxylic acid

C₅₀H₆₇⁽¹⁸⁾FN₈O₁₀