5-(4-aMino-1-isopropyl-1H-pyrazolo[3,4-d]pyriMidin-3-yl)benzo[d]oxazol-2-aMine

Base Information

• Chemical Name: 5-(4-aMino-1-isopropyl-1H-pyrazolo[3,4-d]pyriMidin-3-yl)benzo[d]oxazol-2-aMine
• CAS No.: 1224844-38-5
• Molecular Formula: C15H15N7O
• Molecular Weight: 309.33
• Mol file: 1224844-38-5.mol

Synonyms:INK-128;5-(4-Amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)benzo[d]oxazol-2-amine;

Chemical Property of 5-(4-aMino-1-isopropyl-1H-pyrazolo[3,4-d]pyriMidin-3-yl)benzo[d]oxazol-2-aMine

Chemical Property:

• Boiling Point: 598.8±60.0 °C(Predicted)
• PKA: 3.77±0.30(Predicted)
• PSA: 121.67000
• Density: 1.64
• LogP: 3.54220
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 25 mg/ml)

Purity/Quality:

99% ^*data from raw suppliers

3-(2-Amino-5-benzoxazolyl)-1-(1-methylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: INK128 is an inhibitor of TORC1/2, acting as an ATP-dependent inhibitor of mTOR kinase (IC50 = 1 nM). It blocks the phosphorylation of downstream substrates of both TORC1 and TORC2. INK128 interferes with the growth of cell lines which are resistant to rapamycin and pan-PI3K inhibitors. Moreover, daily, oral administration of INK128 inhibits angiogenesis and tumor growth in several xenograft models. The effects of INK128 on gene expression also reduce invasion and metastasis.
• Uses: 3-(2-Amino-5-benzoxazolyl)-1-(1-methylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine is a potent and selective TORC1/2 inhibitor with broad oral antitumor activity. TORC1/2 inhibitors are mechanistically distinct from rapamycinand offer a compelling approach to the treatment of cancer by targeting translational control, cell metabolism, growth andangiogenesis.

Technology Process of 5-(4-aMino-1-isopropyl-1H-pyrazolo[3,4-d]pyriMidin-3-yl)benzo[d]oxazol-2-aMine

There total 12 articles about 5-(4-aMino-1-isopropyl-1H-pyrazolo[3,4-d]pyriMidin-3-yl)benzo[d]oxazol-2-aMine 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: 95.7%

bromocyane (506-68-3) + 1-isopropyl-3-(4-hydroxy-3-aminophenyl)-1H pyrazolo[3,4-d]pyrimidin-4-amine → INK128 (1224844-38-5)

Guidance literature:

With methanol; at 20 ℃; for 20h; Cooling with ice;

Reference yield: 92.0%

5-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-amine (1224844-66-9) + 1-isopropyl-3-bromo-4-amino-1H-pyrazolo[3,4-d]pyrimidine → INK128 (1224844-38-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 110 ℃; for 2.75h;

DOI:10.1021/acsmedchemlett.9b00401

Reference yield:

2-amino-benzooxazole-5-boronic acid hydrochloride (1404480-15-4) + 1-isopropyl-3-bromo-4-amino-1H-pyrazolo[3,4-d]pyrimidine → INK128 (1224844-38-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 20 - 88 ℃; for 7.5h; Inert atmosphere; Large scale;

upstream raw materials:

2-amino-benzooxazole-5-boronic acid hydrochloride

3-bromo-4-aminopyrazolo<3,4-d>pyrimidine

5-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazol-2-amine

2-amino-4-bromo-phenol

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