9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one

Base Information

• Chemical Name: 9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one
• CAS No.: 1223001-51-1
• Molecular Formula: C24H15F3N4O
• Molecular Weight: 432.405
• Mol file: 1223001-51-1.mol

Synonyms:Torin 2;

Chemical Property of 9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one

Chemical Property:

• Boiling Point: 623.66 °C at 760 mmHg
• PKA: 5.66±0.26(Predicted)
• Flash Point: 330.978 °C
• PSA: 73.80000
• Density: 1.427 g/cm³
• LogP: 5.78310
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

97% ^*data from raw suppliers

Torin 2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Torin 2 is a potent and selective mTOR inhibitor with IC50 of 0.25 nM in p53?/? MEFs cell line; 800-fold greater selectivity for mTOR than PI3K and improved pharmacokinetic properties. Inhibition of ATM/ATR/DNA-PK with EC50 of 28 nM/35 nM/118 nM,in PC3 cell lines respectively. Torin 2 is a potent and selective inhibitor of cellular mTOR activity (EC50 = 0.3 nM). It shows more than 800-fold selectivity for mTOR over PI3K (EC50 = 200 nM) and greater than 100-fold binding selectivity relative to 440 other protein kinases. Torin 2 has significantly improved bioavailability (54%), metabolic stability, and plasma exposure compared to torin 1 .
• Uses: Torin2 has been used:to examine its effect on LC3B-II levels in BORCS5- KO cellsto determine its potent activity (IC50?less than 1 μM) against A2780-cis ovarian cancer cellsin western blot analysis Torin 2 is a potent, selective, and orally available mammalian target of rapamycin (mTOR) inhibitor for treatment of cancer.

Technology Process of 9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one

There total 11 articles about 9-(6-Amino-3-pyridinyl)-1-[3-(trifluoromethyl)phenyl]benzo[h]-1,6-naphthyridin-2(1H)-one 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: 90.0%

2-aminopyridine-5-boronic acid pinacol ester (827614-64-2) + 3-(6-bromo-4-chloroquinolin-3-yl)acrylate + 3-trifluoromethylaniline (98-16-8) → Torin2 (1223001-51-1)

Guidance literature:

3-(6-bromo-4-chloroquinolin-3-yl)acrylate; 3-trifluoromethylaniline; With hydrogenchloride; In 1,4-dioxane; N,N-dimethyl-formamide; at 100 ℃; for 0.25h; Microwave irradiation;

2-aminopyridine-5-boronic acid pinacol ester; With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; N,N-dimethyl-formamide; isopropyl alcohol; at 150 ℃; for 0.166667h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Microwave irradiation;

DOI:10.1021/acscombsci.7b00119

Reference yield:

9-bromo-1-(3-(trifluoromethyl)phenyl)benzo[h][1,6]naphthyridin-2(1H)-one → Torin2 (1223001-51-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; at 100 ℃; for 15h; Sealed tube; Inert atmosphere;

DOI:10.3390/molecules23050992

Reference yield:

1-(2-amino-5-bromophenyl)ethanone (29124-56-9) → Torin2 (1223001-51-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trichlorophosphate / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 4 h / 60 °C / Inert atmosphere

2.1: potassium carbonate; 18-crown-6 ether / tetrahydrofuran / 1 h / 0 °C

3.1: hydrogenchloride / N,N-dimethyl-formamide; 1,4-dioxane / 0.25 h / 100 °C / Microwave irradiation

3.2: 0.17 h / 150 °C / Inert atmosphere; Microwave irradiation

With hydrogenchloride; 18-crown-6 ether; potassium carbonate; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/acscombsci.7b00119

upstream raw materials:

1-(2-amino-5-bromophenyl)ethanone

6-bromo-4-chloroquinoline-3-carbaldehyde

2-aminopyridine-5-boronic acid pinacol ester

3-trifluoromethylaniline