2-[[5-(2,6-Dimethoxyphenyl)-1-[4-[3-(dimethylamino)propyl-methylcarbamoyl]-2-propan-2-ylphenyl]pyrazole-3-carbonyl]amino]adamantane-2-carboxylic acid

Base Information

• Chemical Name: 2-[[5-(2,6-Dimethoxyphenyl)-1-[4-[3-(dimethylamino)propyl-methylcarbamoyl]-2-propan-2-ylphenyl]pyrazole-3-carbonyl]amino]adamantane-2-carboxylic acid
• CAS No.: 184162-64-9
• Molecular Formula: C39H51N5O6
• Molecular Weight: 685.85214
• UNII: W59C8B2MZS
• DSSTox Substance ID: DTXSID50415529
• Nikkaji Number: J822.698I
• Wikipedia: SR-142948
• Wikidata: Q7392758
• Pharos Ligand ID: 3G3G16STAYP7
• ChEMBL ID: CHEMBL3040381
• Mol file: 184162-64-9.mol

Synonyms:SR 142948;SR-142948

Chemical Property of 2-[[5-(2,6-Dimethoxyphenyl)-1-[4-[3-(dimethylamino)propyl-methylcarbamoyl]-2-propan-2-ylphenyl]pyrazole-3-carbonyl]amino]adamantane-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 8.51E-29mmHg at 25°C
• Boiling Point: 824.7°C at 760 mmHg
• Flash Point: 452.5°C
• PSA: 129.72000
• Density: 1.29g/cm³
• LogP: 6.28770
• Storage Temp.: Store at +4°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 685.38393436
• Heavy Atom Count: 50
• Complexity: 1170

Purity/Quality:

97% ^*data from raw suppliers

SR 142948 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C=CC(=C1)C(=O)N(C)CCCN(C)C)N2C(=CC(=N2)C(=O)NC3(C4CC5CC(C4)CC3C5)C(=O)O)C6=C(C=CC=C6OC)OC
• Uses: SR 142948 is an antagonist of NT1/NT2 receptors inhibiting bile acid secretion. Neurotensin receptor antagonist.

Technology Process of 2-[[5-(2,6-Dimethoxyphenyl)-1-[4-[3-(dimethylamino)propyl-methylcarbamoyl]-2-propan-2-ylphenyl]pyrazole-3-carbonyl]amino]adamantane-2-carboxylic acid

There total 7 articles about 2-[[5-(2,6-Dimethoxyphenyl)-1-[4-[3-(dimethylamino)propyl-methylcarbamoyl]-2-propan-2-ylphenyl]pyrazole-3-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: 57.0%

2-({[1-(4-bromo-2-isopropylphenyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-yl]carbonyl}amino)adamantane-2-carboxylic acid (1476064-46-6) + N,N,N'-trimethylpropane-1,3-diamine (4543-96-8) + molybdenum hexacarbonyl (13939-06-5,199620-15-0) → 2-[({5-(2,6-dimethoxyphenyl)-1-[4-({[3-(dimethylamino)propyl](methyl)amino}carbonyl)-2-isopropylphenyl]-1H-pyrazol-3-yl}carbonyl)amino]adamantane-2-carboxylic acid (184162-64-9)

Guidance literature:

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; Inert atmosphere; Sealed tube; Microwave irradiation;

DOI:10.1055/s-0033-1338497

Reference yield:

2-isopropylaniline (643-28-7) → 2-[({5-(2,6-dimethoxyphenyl)-1-[4-({[3-(dimethylamino)propyl](methyl)amino}carbonyl)-2-isopropylphenyl]-1H-pyrazol-3-yl}carbonyl)amino]adamantane-2-carboxylic acid (184162-64-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ammonium acetate; N-Bromosuccinimide / acetonitrile / 0.17 h / 20 °C

2.1: hydrogenchloride; sodium nitrite / water / 0 °C

2.2: 0.5 h / 0 °C

2.3: 0.33 h / Reflux

3.1: potassium hydroxide; water / 1,4-dioxane / 4 h / Reflux

4.1: triethylamine; isobutyl chloroformate / acetonitrile / 0.42 h / 20 °C / Inert atmosphere

4.2: 2 h / 60 °C / Inert atmosphere; Microwave irradiation

5.1: 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; Sealed tube; Microwave irradiation

With hydrogenchloride; N-Bromosuccinimide; trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); ammonium acetate; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium hydroxide; tri tert-butylphosphoniumtetrafluoroborate; sodium nitrite; isobutyl chloroformate; In 1,4-dioxane; water; acetonitrile;

DOI:10.1055/s-0033-1338497

Reference yield:

2-(amino)tricyclo[3.3.1.13,7]decane-2-carboxylic acid hydrochloride (50294-51-4) → 2-[({5-(2,6-dimethoxyphenyl)-1-[4-({[3-(dimethylamino)propyl](methyl)amino}carbonyl)-2-isopropylphenyl]-1H-pyrazol-3-yl}carbonyl)amino]adamantane-2-carboxylic acid (184162-64-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / acetonitrile / 0.08 h / 20 °C / Inert atmosphere

2.1: triethylamine; isobutyl chloroformate / acetonitrile / 0.42 h / 20 °C / Inert atmosphere

2.2: 2 h / 60 °C / Inert atmosphere; Microwave irradiation

3.1: 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; Sealed tube; Microwave irradiation

With trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; tri tert-butylphosphoniumtetrafluoroborate; isobutyl chloroformate; In 1,4-dioxane; acetonitrile;

DOI:10.1055/s-0033-1338497

upstream raw materials:

1-(4-bromo-2-isopropylphenyl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid

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

N,N,N'-trimethylpropane-1,3-diamine

molybdenum hexacarbonyl

Downstream raw materials:

5-(2,6-dimethoxy-phenyl)-1-{4-[(3-dimethylamino-propyl)-methyl-carbamoyl]-2-isopropyl-phenyl}-1H-pyrazole-3-carboxylic acid [2-(2-DOTA(tBu₃)-ammo-ethylcarbamoyl)-adamantan-2-yl]-amide