(S)-4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol

Base Information

• Chemical Name: (S)-4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol
• CAS No.: 937174-76-0
• Deprecated CAS: 1000873-82-4
• Molecular Formula: C21H27N7O3
• Molecular Weight: 425.49
• Hs Code.: 2934999090
• European Community (EC) Number: 804-554-1
• UNII: GWH480321B
• ChEMBL ID: CHEMBL494089
• DSSTox Substance ID: DTXSID60239551
• Metabolomics Workbench ID: 153677
• NCI Thesaurus Code: C71711
• Nikkaji Number: J2.843.857E
• Pharos Ligand ID: 88VN685LWBR4
• Wikidata: Q27077916
• Mol file: 937174-76-0.mol

Synonyms:GSK690693

Chemical Property of (S)-4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol

Chemical Property:

• Boiling Point: 683.8 °C at 760 mmHg
• PKA: 13.11±0.29(Predicted)
• Flash Point: 367.3 °C
• PSA: 137.14000
• Density: 1.41 g/cm³
• LogP: 2.49420
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble5mg/mL (clear solution)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 425.21753775
• Heavy Atom Count: 31
• Complexity: 680

Purity/Quality:

98%,99%, ^*data from raw suppliers

GSK690693 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C2=C(C(=NC=C2OCC3CCCNC3)C#CC(C)(C)O)N=C1C4=NON=C4N
• Isomeric SMILES: CCN1C2=C(C(=NC=C2OC[C@H]3CCCNC3)C#CC(C)(C)O)N=C1C4=NON=C4N
• Recent ClinicalTrials: Open-label Study to Investigate the Safety, Tolerability, PK, and Pharmacodynamics of the AKT Inhibitor GSK690693
• Description: GSK690693 is an ATP-competitive, pan-Akt kinase inhibitor with IC50 values of 2, 13, and 9 nM for Akt1, 2, and 3, respectively. It also inhibits other members of the AGC kinase family, including AMPK, DAPK3, PAKs, PKA, PKC, PKG, and PrkX (IC50 values range from 2-81 nM). By preventing the phosphorylation of downstream Akt substrates, GSK690693 has been shown to inhibit proliferation and to induce apoptosis in various human tumor cells in vitro and in xenografts in immunocompromised mice.
• Uses: GSK690693 is a pan-Akt inhibitor targeting Akt1, Akt2 and Akt3 with IC50 of 2 nM, 13 nM, and 9 nM, respectively GSK690693 has been used in western blotting and immunoprecipitations.

Technology Process of (S)-4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol

There total 12 articles about (S)-4-(2-(4-Amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-(piperidin-3-ylmethoxy)-1H-imidazo[4,5-c]pyridin-4-yl)-2-methylbut-3-yn-2-ol 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: 93.0%

1,1-dimethylethyl (3S)-3-({[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-4-(3-hydroxy-3-methyl-1-butyn-1-yl)-1H-imidazo[4,5-c]pyridin-7-yl]oxy}methyl)-1-piperidinecarboxylate (937174-75-9) → GSK690693 (937174-76-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/jm8004527

Reference yield:

ethyl-(3-bromo-5-nitropyridin-4-yl)amine (607371-01-7) → GSK690693 (937174-76-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: hydrogenchloride; water; tin(ll) chloride / 85 °C / Heating / reflux

1.2: 0 °C / pH 12

2.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C

3.1: acetic acid / 3 h / 100 °C

4.1: sodium nitrate / 16 h / 20 °C

5.1: hydroxylamine hydrochloride; triethylamine / 1,4-dioxane; water / 6 h / Heating / reflux

6.1: methanol / 0.5 h / 65 °C

7.1: isopropyl magnesium chloride / tetrahydrofuran; diethyl ether / 0.17 h / -75 - -70 °C / Cooling with acetone-dry ice

7.2: 19 h / 20 °C / Cooling with acetone-dry ice

8.1: caesium carbonate / N,N-dimethyl-formamide / 26 h / 35 - 40 °C

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; zinc / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dimethyl sulfoxide / 4.17 h / 80 °C

10.1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; sodium nitrate; hydroxylamine hydrochloride; water; caesium carbonate; isopropyl magnesium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; sodium iodide; tin(ll) chloride; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

5-bromo-2-chloro-N4-ethylpyridine-3,4-diamine (842144-03-0) → GSK690693 (937174-76-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C

2.1: acetic acid / 3 h / 100 °C

3.1: sodium nitrate / 16 h / 20 °C

4.1: hydroxylamine hydrochloride; triethylamine / 1,4-dioxane; water / 6 h / Heating / reflux

5.1: methanol / 0.5 h / 65 °C

6.1: isopropyl magnesium chloride / tetrahydrofuran; diethyl ether / 0.17 h / -75 - -70 °C / Cooling with acetone-dry ice

6.2: 19 h / 20 °C / Cooling with acetone-dry ice

7.1: caesium carbonate / N,N-dimethyl-formamide / 26 h / 35 - 40 °C

8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium iodide; zinc / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dimethyl sulfoxide / 4.17 h / 80 °C

9.1: trifluoroacetic acid / dichloromethane / 2.5 h / 20 °C

With 4-methyl-morpholine; sodium nitrate; hydroxylamine hydrochloride; caesium carbonate; isopropyl magnesium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; sodium iodide; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

1,1-dimethylethyl (3S)-3-({[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-4-(3-hydroxy-3-methyl-1-butyn-1-yl)-1H-imidazo[4,5-c]pyridin-7-yl]oxy}methyl)-1-piperidinecarboxylate

ethyl-(3-bromo-5-nitropyridin-4-yl)amine

5-bromo-2-chloro-N₄-ethylpyridine-3,4-diamine

(7-bromo-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)acetonitrile

Refernces

• 1、 -. "METHODS OF USE FOR INHIBITORS OF AKT ACTIVITY". Page/Page column 39. . Retrieved 2008/12/04.