1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol

Base Information

• Chemical Name: 1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol
• CAS No.: 1394121-05-1
• Molecular Formula: C₂₂H₂₆N₆O₂
• Molecular Weight: 406.487
• Mol file: 1394121-05-1.mol

Synonyms:1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol

Chemical Property of 1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

GNE2861 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol

There total 6 articles about 1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-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: 37.0%

1-(2-aminopyrimidin-4-yl)-6-bromo-N-(2-methoxyethyl)-1H-1,3-benzodiazol-2-amine (1394120-96-7) + 1-Ethynylcyclohexan-1-ol (78-27-3) → 1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol (1394121-05-1)

Guidance literature:

With trans-bis(triphenylphosphine)palladium dichloride; triethylamine; In dimethyl sulfoxide; at 70 ℃; for 0.333333h; Microwave irradiation; Inert atmosphere;

DOI:10.1021/jm401768t

Reference yield:

4-bromo-2-fluoronitrobenzene (321-23-3) → 1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol (1394121-05-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 - 20 °C

1.2: 1 h / 65 °C

2.1: ammonium hydroxide / isopropyl alcohol / 20 h / 20 - 90 °C / Sealed vial

3.1: tin(ll) chloride / ethanol / 2 h / 65 °C

4.1: 20 - 45 °C

5.1: 72 h / 20 °C

6.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 1 h / 70 °C / Inert atmosphere

With ammonium hydroxide; sodium hydride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; tin(ll) chloride; In tetrahydrofuran; ethanol; dimethyl sulfoxide; isopropyl alcohol;

Reference yield:

2-(trichloromethyl)benzimidazole (1394120-92-3) → 1-[2-[1-(2-aminopyrimidin-4-yl)-2-[(2-methoxyethyl)amino]-1H-1,3-benzodiazol-6-yl]ethynyl]cyclohexan-1-ol (1394121-05-1)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / 20 °C

2: trans-bis(triphenylphosphine)palladium dichloride; triethylamine / dimethyl sulfoxide / 0.33 h / 70 °C / Microwave irradiation; Inert atmosphere

With trans-bis(triphenylphosphine)palladium dichloride; caesium carbonate; triethylamine; In dimethyl sulfoxide; 2: |Sonogashira Cross-Coupling;

DOI:10.1021/jm401768t

upstream raw materials:

1-(2-aminopyrimidin-4-yl)-6-bromo-N-(2-methoxyethyl)-1H-1,3-benzodiazol-2-amine

1-Ethynylcyclohexan-1-ol

N₄-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine

2-(trichloromethyl)benzimidazole

Refernces

• 1、 -. "SERINE/THREONINE KINASE INHIBITORS". Page/Page column 38-39. . Retrieved 2014/11/11.