ON123300

Base Information

• Chemical Name: ON123300
• CAS No.: 1357470-29-1
• Molecular Formula: C24H27N7O
• Molecular Weight: 429.52
• Mol file: 1357470-29-1.mol

Synonyms:ON123300;8-Cyclopentyl-7,8-dihydro-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-7-oxo-pyrido[2,3-d]pyrimidine-6-carbonitrile

Chemical Property of ON123300

Chemical Property:

• Boiling Point: 642.7±65.0 °C(Predicted)
• PKA: 7.88±0.42(Predicted)
• PSA: 90.08000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 3.34958
• Solubility.: ≥21.5 mg/mL in DMSO with gentle warming; insoluble in EtOH; insoluble in H2O

Purity/Quality:

98% min ^*data from raw suppliers

ON123300 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: ON123300 is a potent multikinase inhibitor and may be potential useful for brain tumor chemotherapy. ON123300 strongly inhibits Ark5 and CDK4, as well as growth factor receptor tyrosine kinases.

Technology Process of ON123300

There total 13 articles about ON123300 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: 55.0%

4-(4-Methyl-piperazino)-anilin (16153-81-4) + 8-cyclopentyl-2-methanesulfinyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile → 8-cyclopentyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (1357470-29-1)

Guidance literature:

In toluene; at 100 ℃;

DOI:10.1021/jm401073p

Reference yield:

Cyclopentamine (1003-03-8) → 8-cyclopentyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (1357470-29-1)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / tetrahydrofuran / 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / -20 - 20 °C / Inert atmosphere

3: manganese(IV) oxide / chloroform / 12 h

4: acetic acid / benzylamine / 6 h / Reflux

5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C

6: toluene / 100 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; benzylamine; In tetrahydrofuran; dichloromethane; chloroform; toluene;

Reference yield:

4-cyclopentylamino-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester (211245-62-4) → 8-cyclopentyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (1357470-29-1)

Guidance literature:

Multi-step reaction with 5 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / -20 - 20 °C / Inert atmosphere

2: manganese(IV) oxide / chloroform / 12 h

3: acetic acid / benzylamine / 6 h / Reflux

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C

5: toluene / 100 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; benzylamine; In tetrahydrofuran; dichloromethane; chloroform; toluene;

upstream raw materials:

Cyclopentamine

4-(4-Methyl-piperazino)-anilin

4-cyclopentylamino-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester

4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde

Refernces

• 1、 -. "2-SUBSTITUTED-8-ALKYL-7-OXO-7,8-DIHYDROPYRIDO[2,3-D] PYRIMIDINE-6-CARBONITRILES AND USES THEREOF". . . Retrieved 2012/02/15.