OSI-027

Base Information

• Chemical Name: OSI-027
• CAS No.: 936890-98-1
• Molecular Formula: C₂₁H₂₂N₆O₃
• Molecular Weight: 406.444
• Mol file: 936890-98-1.mol

Synonyms:K1146_Kinasechem;Cyclohexanecarboxylic acid,4-(4-amino-5-(7-methoxy-1H-indol-2-yl)imidazo(5,1-f)(1,2,4)triazin-7-yl)-,trans;OSI-027;UNII-25MKH1SZ0M;OSI027,OSI-027;

Chemical Property of OSI-027

Chemical Property:

• PKA: 4.44±0.10(Predicted)
• PSA: 131.42000
• Density: 1.59
• LogP: 3.80300
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

4-(4-Amino-5-(7-methoxy-1H-indol-2-yl)imidazo[5,1-f][1,2,4]Triazin-7-yl)cyclohexanecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: The mammalian target of rapamycin (mTOR) is a serine-threonine kinase that is central to two protein complexes, mTORC1 and mTORC2. These complexes are differentially regulated (e.g., only mTORC1 is sensitive to rapamycin ) and regulate different pathways. OSI-027 is an inhibitor of the catalytic site of mTOR and, as a result, inhibits both mTORC1 and mTORC2 (IC50s = 22 and 65 nM, respectively). It is selective for mTOR over phosphatidylinositol 3-kinase isoforms and DNA protein kinase. OSI-027 prohibits proliferation, induces autophagy, and potentiates apoptosis in BCR-ABL transformed cells and other cancer cells at 10 μM. OSI-027 is effective in vivo, blocking the phosphorylation of targets of mTORC1 and mTORC2 and suppressing tumor growth in several different human xenograft models.
• Uses: OSI-027 is a kinase inhibitor with anti-tumor activity, used in treatment of breast cancer.

Technology Process of OSI-027

There total 8 articles about OSI-027 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: 77.0%

7-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (1072812-69-1) + trans-4-(4-amino-5-bromoimidazo[5,1-f][1,2,4]triazin-7-yl)cyclohexanecarboxylic acid (1260585-96-3) → OSI-027 (936890-98-1)

Guidance literature:

trans-4-(4-amino-5-bromoimidazo[5,1-f][1,2,4]triazin-7-yl)cyclohexanecarboxylic acid; With sodium carbonate; In ethanol; water; at 20 ℃; for 0.666667h; Industry scale; Inert atmosphere;

7-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole; With bis(p-sulfonatophenyl)phenylphosphinedihydrate dipotassium salt; palladium diacetate; In ethanol; water; at 60 ℃; for 7h; Industry scale; Inert atmosphere;

With hydrogenchloride; In water; pH=5 - 6; Industry scale;

Reference yield:

3-amino-6-((dibenzylamino)methyl)-1,2,4-triazine-5-(4H)-one (93206-03-2) → OSI-027 (936890-98-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogen; acetic acid / palladium 10% on activated carbon / water / 55 °C / Industry scale; Inert atmosphere

1.2: Industry scale

1.3: 50 °C / Industry scale

2.1: trichlorophosphate / acetonitrile / Reflux; Industry scale

2.2: 1 h / 0 - 30 °C / pH 8 / Industry scale

3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 - 37 °C / Industry scale

4.1: tert.-butylnitrite / tetrahydrofuran / 15 - 25 °C / Industry scale

5.1: trichlorophosphate; 1,2,4-Triazole / pyridine / 10 - 40 °C / Industry scale

5.2: -15 - 0 °C / Industry scale

6.1: sodium carbonate / ethanol; water / 0.67 h / 20 °C / Industry scale; Inert atmosphere

6.2: 7 h / 60 °C / Industry scale; Inert atmosphere

6.3: pH 5 - 6 / Industry scale

With 1,2,4-Triazole; N-Bromosuccinimide; tert.-butylnitrite; hydrogen; sodium carbonate; acetic acid; trichlorophosphate; palladium 10% on activated carbon; In tetrahydrofuran; pyridine; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

dibenzylamine (103-49-1) → OSI-027 (936890-98-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: ethyl acetate / 60 - 80 °C / Industry scale

1.2: 24 h / Reflux; Industry scale

2.1: hydrogen; acetic acid / palladium 10% on activated carbon / water / 55 °C / Industry scale; Inert atmosphere

2.2: Industry scale

2.3: 50 °C / Industry scale

3.1: trichlorophosphate / acetonitrile / Reflux; Industry scale

3.2: 1 h / 0 - 30 °C / pH 8 / Industry scale

4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 - 37 °C / Industry scale

5.1: tert.-butylnitrite / tetrahydrofuran / 15 - 25 °C / Industry scale

6.1: trichlorophosphate; 1,2,4-Triazole / pyridine / 10 - 40 °C / Industry scale

6.2: -15 - 0 °C / Industry scale

7.1: sodium carbonate / ethanol; water / 0.67 h / 20 °C / Industry scale; Inert atmosphere

7.2: 7 h / 60 °C / Industry scale; Inert atmosphere

7.3: pH 5 - 6 / Industry scale

With 1,2,4-Triazole; N-Bromosuccinimide; tert.-butylnitrite; hydrogen; sodium carbonate; acetic acid; trichlorophosphate; palladium 10% on activated carbon; In tetrahydrofuran; pyridine; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

dibenzylamine

trans-4-(2-amino-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-7-yl)cyclohexanecarboxylic acid methyl ester

trans-4-[(3-amino-5-oxo-4,5-dihydro[1,2,4]triazin-6-ylmethyl)carbamoyl]cyclohexanecarboxylic acid methyl ester

trans-4-(2-amino-5-bromo-4-oxo-3,4-dihydroimidazo[5,1-f][1,2,4]triazin-7-yl)cyclohexanecarboxylic acid methyl ester

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