1-(4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone

Base Information

• Chemical Name: 1-(4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone
• CAS No.: 1227067-61-9
• Molecular Formula: C₂₅H₂₃N₅O₃
• Molecular Weight: 441.489
• Mol file: 1227067-61-9.mol

Synonyms:1-(4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone

Chemical Property of 1-(4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone

Chemical Property:

• Boiling Point: 689.9±65.0 °C(Predicted)
• Density: 1.322±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

AMG579 99.79% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone

There total 7 articles about 1-(4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone 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: 87.0%

(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (1227060-00-5) + 1-(4-(3-fluoropyrazin-2-yl)piperidin-1-yl)ethanone (1227068-57-6) → 1-(4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone (1227067-61-9)

Guidance literature:

With caesium carbonate; In 1-methyl-pyrrolidin-2-one; at 120 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jm500713j

Reference yield:

benzyl 4-(3-fluoropyrazin-2-yl)piperidine-1-carboxylate → 1-(4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone (1227067-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 20% palladium hydroxide-activated charcoal; hydrogen / toluene / 9.16 h / 10 °C

2: caesium carbonate / 1-methyl-pyrrolidin-2-one / 5 h / 120 °C / Inert atmosphere

With 20% palladium hydroxide-activated charcoal; hydrogen; caesium carbonate; In 1-methyl-pyrrolidin-2-one; toluene;

DOI:10.1021/jm500713j

Reference yield:

1-(benzyloxycarbonyl)-4-hydroxypiperidine (95798-23-5) → 1-(4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone (1227067-61-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 18.33 h / 0 - 20 °C

2.1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 0.5 h / 20 °C

2.2: 1.25 h / 20 - 80 °C

3.1: 20% palladium hydroxide-activated charcoal; hydrogen / toluene / 9.16 h / 10 °C

4.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 5 h / 120 °C / Inert atmosphere

With 1H-imidazole; chloro-trimethyl-silane; 20% palladium hydroxide-activated charcoal; hydrogen; iodine; caesium carbonate; ethylene dibromide; triphenylphosphine; zinc; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; N,N-dimethyl acetamide; toluene; 2.1: |Negishi Coupling;

DOI:10.1021/jm500713j

upstream raw materials:

(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone

1-(4-(3-fluoropyrazin-2-yl)piperidin-1-yl)ethanone

1-(benzyloxycarbonyl)-4-hydroxypiperidine

4-iodo-piperidine-1-carboxylic acid benzyl ester

Downstream raw materials:

1-(4-(3-(4-((1H-benzo[d]imidazol-2-yl)(hydroxy)methyl)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone

Refernces

• 1、 -. "PYRAZINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS". Page/Page column 201. . Retrieved 2010/06/15.