(5R)-5-ethyl-3-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione

Base Information

• Chemical Name: (5R)-5-ethyl-3-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione
• CAS No.: 1311136-84-1
• Molecular Formula: C₁₈H₁₉N₃O₄
• Molecular Weight: 341.367
• Mol file: 1311136-84-1.mol

Synonyms:(5R)-5-ethyl-3-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione

Chemical Property of (5R)-5-ethyl-3-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione

Chemical Property:

Purity/Quality:

99%+, ^*data from raw suppliers

(5R)-5-Ethyl-3-[6-(3-methoxy-4-methylphenoxy)-3-pyridinyl]-2,4-imidazolidinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: AUT1 is a positive modulator of the voltage-gated potassium channel subtypes Kv3.1b, Kv3.2a, and Kv3.3 (EC50s = 4.7, 4.9, and 31.6 μM, respectively, in a patch-clamp assay). It is selective for Kv3.1b, Kv3.2a, and Kv3.3 over Kv1.5 and Kv7.1/minK channels but also inhibits the serotonin (5-HT) transporter, 5-HT3 receptor, and α1 subunit-containing nicotinic acetylcholine receptor (nAChR) in a panel of 26 ion channels, receptors, and transporters. AUT1 increases tetraethylammonium-induced decreases in the firing frequency and amplitude of action potentials in mouse somatosensory cortex slices when used at concentrations of 1 and 10 μM.
• Uses: (5R)-5-Ethyl-3-[6-(3-methoxy-4-methylphenoxy)-3-pyridinyl]-2,4-imidazolidinedione, is a novel modulator of Kv3 potassium channels which biological studies have shown it regulates the firing of parvalbumin-positive cortical interneurons.

Technology Process of (5R)-5-ethyl-3-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione

There total 8 articles about (5R)-5-ethyl-3-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione 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:

bis(trichloromethyl) carbonate (32315-10-9) + (2R)-2-amino-N-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)butanamide (1311138-23-4) → (5R)-5-ethyl-3-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione (1311136-84-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

Reference yield:

bis(trichloromethyl) carbonate (32315-10-9) + (2R)-2-amino-N-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)butanamide dihydrochloride → (5R)-5-ethyl-3-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione (1311136-84-1)

Guidance literature:

(2R)-2-amino-N-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)butanamide dihydrochloride; With sodium carbonate; In dichloromethane; water;

bis(trichloromethyl) carbonate; With triethylamine; In dichloromethane; at 0 - 10 ℃;

Reference yield:

4-methyl-3-(methyloxy)phenol (19217-50-6) → (5R)-5-ethyl-3-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione (1311136-84-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 115 °C

2.1: water; ammonium chloride / iron / tetrahydrofuran / 8 h / 20 °C

3.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.25 h / 20 °C

3.2: 20 °C

4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

5.1: triethylamine / dichloromethane / 0.5 h / 0 °C

With water; potassium carbonate; ammonium chloride; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; iron; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

4-methyl-3-(methyloxy)phenol

ortho-cresidine

bis(trichloromethyl) carbonate

(2R)-2-amino-N-(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)butanamide

Refernces

• 1、 -. "IMIDAZOLIDINEDIONE DERIVATIVES". . . Retrieved 2011/06/26.