CHIR-258

Base Information

• Chemical Name: CHIR-258
• CAS No.: 804551-71-1
• Molecular Formula: C₂₁H₂₁FN₆O
• Molecular Weight: 392.436
• Mol file: 804551-71-1.mol

Synonyms:4-Amino-5-fluoro-3-[6-(4-methyl-1-piperazinyl)-1H-benzimidazol-2-yl]-2(1H)-quinolinone 2-hydroxypropanoate hydrate (1:1:1); 4-amino-5-fluoro-3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]quinolin-2(1H)-one

Chemical Property of CHIR-258

Chemical Property:

• PSA: 94.30000
• LogP: 3.54090

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CHIR-258

There total 7 articles about CHIR-258 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: 88.4%

[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]acetic acid ethyl ester (402948-37-2) + 2-amino-6-fluorobenzonitrile (77326-36-4) → 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one (405169-16-6,804551-71-1)

Guidance literature:

[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]acetic acid ethyl ester; 2-amino-6-fluorobenzonitrile; In toluene; at 20 - 65 ℃; for 2h; Inert atmosphere;

With potassium tert-butylate; In toluene; at 50 ℃; for 2h; Temperature;

Reference yield: 60.0%

ethyl 2-[5-(4-methylpiperazinyl)benzimidazol-2-yl]acetate + 2-amino-6-fluorobenzonitrile (77326-36-4) → 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one (405169-16-6,804551-71-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2005.11.113

Reference yield:

5-chloro-2-nitroaniline (1635-61-6) → 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one (405169-16-6,804551-71-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / ethanol / 40 h / 97 °C

2: H₂ / Pd/C / aq. ethanol / 6 h / 40 - 50 °C

3: 1.98 kg / aq. ethanol / 2 h

4: 85.4 percent / KOt-Bu / tetrahydrofuran; toluene / 2 h / 17 - 30 °C

With potassium tert-butylate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; toluene;

DOI:10.2533/chimia.2006.584

upstream raw materials:

2-amino-6-fluorobenzonitrile

[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]acetic acid ethyl ester

1-methyl-piperazine

5-chloro-2-nitroaniline