AZD-8055

Base Information

• Chemical Name: AZD-8055
• CAS No.: 1009298-09-2
• Molecular Formula: C₂₅H₃₁N₅O₄
• Molecular Weight: 465.552
• Hs Code.: 29335990
• Mol file: 1009298-09-2.mol

Synonyms:AZD 8055;[5-[2,4-Bis((3S)-3-methylmorpholin-4-yl)pyrido[2,3-d]pyrimidin-7-yl]-2-methoxyphenyl]methanol;

Chemical Property of AZD-8055

Chemical Property:

• Boiling Point: 694.302 °C at 760 mmHg
• PKA: 14.20±0.10(Predicted)
• Flash Point: 373.701 °C
• PSA: 93.07000
• Density: 1.248 g/cm³
• LogP: 2.77290
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 30 mg/ml)

Purity/Quality:

99% ^*data from raw suppliers

AZD8055 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: AZD8055 (1009298-09-2) is a potent and highly selective inhibitor of mammalian target of rapamycin kinase (mTOR) kinase (IC50 = 0.8 nM).1,2 ?mTOR acts as a nutrient/energy/redox sensor and a controller of protein synthesis – as such it is a very important target for cancer research.? It has been investigated as a potential chemotherapeutic for various cancers.3-7
• Uses: A novel ATP-competitive inhibitor of mTOR with an IC50 of 0.8 nM. A potent, selective, and orally bioavailable ATP-competitive mTOR kinase inhibitor with an IC50 of 0.8 nM. It inhibits the phosphorylation of mTORC1 substrates p70S6K and 4E-BP1 as well as phosphoryla tion of the mTORC2 substrate AKT and downstream proteins. The rapamycin-resistant T37/46 phosphorylation sites on 4E-BP1 were fully inhibited by AZD8055, resulting in significant inhibition of cap-dep endent translation. In vitro, AZD8055 potently inhibits proliferation and induces autophagy in H838 and A549 cells. In vivo, AZD8055 induces a dose-dependent pharmacodynamic effect on phosphorylated S 6 and phosphorylated AKT at plasma concentrations leading to tumor growth inhibition.

Technology Process of AZD-8055

There total 10 articles about AZD-8055 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:

2-amino-6-chloro-pyridine-3-carboxamide (64321-24-0) → AZD8055 (1009298-09-2)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene / 115 °C

2: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / 100 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 70 °C

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In dichloromethane; N,N-dimethyl acetamide; toluene;

DOI:10.1016/j.bmcl.2013.01.019

Reference yield:

(3S)-4-[7-chloro-2-[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d] pyrimidin-4-yl] 3-methyl-morpholine (1009303-44-9) + [2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol (1009303-77-8) → AZD8055 (1009298-09-2)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; toluene; at 140 ℃; for 0.5h; Microwave radiation;

Reference yield:

methyl 5-{2,4-bis[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d]pyrimidin-7-yl}-2-methoxybenzoate (1009298-82-1) → AZD8055 (1009298-09-2)

Guidance literature:

methyl 5-{2,4-bis[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d]pyrimidin-7-yl}-2-methoxybenzoate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 16h; Inert atmosphere;

With water; In tetrahydrofuran;

upstream raw materials:

(3S)-4-[7-chloro-2-[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d] pyrimidin-4-yl] 3-methyl-morpholine

[2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol

methyl 5-{2,4-bis[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d]pyrimidin-7-yl}-2-methoxybenzoate

5-{2,4-bis[(3S)-3-methylmorpholin-4-yl]pyrido[2,3-d]pyrimidin-7-yl}-2-methoxybenzyl pivalate

Refernces

• 1、 -. "COMPOSITION AND PROCESS - 356". Page/Page column 33-34. . Retrieved 2009/12/28.