VU 0409551

Base Information

• Chemical Name: VU 0409551
• CAS No.: 1363281-27-9
• Molecular Formula: C₂₀H₁₇FN₂O₃
• Molecular Weight: 352.365
• Mol file: 1363281-27-9.mol

Synonyms:(4-fluorophenyl)-[2-(phenoxymethyl)-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl]methanone

Chemical Property of VU 0409551

Chemical Property:

• Boiling Point: 545.8±50.0 °C(Predicted)
• PKA: 1.35±0.20(Predicted)
• Density: 1.308±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

VU0409551 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: VU 0409551 is an mGlu5 allosteric modulator.

Technology Process of VU 0409551

There total 14 articles about VU 0409551 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: 88.0%

2-(phenoxymethyl)-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridine (1363286-28-5) + 4-fluorobenzoyl chloride (403-43-0) → (4-fluorophenyl)-[2-(phenoxymethyl)-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl]methanone (1363281-27-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/acsmedchemlett.5b00181

Reference yield:

Phenoxyacetyl chloride (701-99-5) → (4-fluorophenyl)-[2-(phenoxymethyl)-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl]methanone (1363281-27-9)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 1 h / 0 - 20 °C

2: Dess-Martin periodane / dichloromethane / 16 h / 20 °C

3: trichlorophosphate / 1,4-dioxane / 2 h / 100 °C

4: water; lithium hydroxide / 1,4-dioxane / 90 h / 125 °C / Inert atmosphere

5: triethylamine / dichloromethane / 0.25 h / 0 - 20 °C

With water; Dess-Martin periodane; triethylamine; lithium hydroxide; trichlorophosphate; In 1,4-dioxane; dichloromethane;

Reference yield:

ethyl 3-bromo-4-oxo-1-piperidinecarboxylate (95629-02-0) → (4-fluorophenyl)-[2-(phenoxymethyl)-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl]methanone (1363281-27-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 60 h / 125 °C / silica gel

2: 4-methylmorpholine N-oxide / osmium(VIII) oxide / water; tert-butyl alcohol; tetrahydrofuran; methanol / 16 h / 20 °C

3: sodium periodate / water; tetrahydrofuran; methanol / 2 h / 20 °C

4: sodium tetrahydroborate; methanol / 0.33 h / 0 - 20 °C

5: triphenylphosphine; di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 0.33 h / 0 - 20 °C

6: water; lithium hydroxide / 1,4-dioxane / 90 h / 125 °C / Inert atmosphere

7: triethylamine / dichloromethane / 0.25 h / 0 - 20 °C

With methanol; sodium tetrahydroborate; sodium periodate; di-tert-butyl-diazodicarboxylate; water; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; lithium hydroxide; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; tert-butyl alcohol;

upstream raw materials:

ethyl 3-bromo-4-oxo-1-piperidinecarboxylate

2-(phenoxymethyl)-4,5,6,7-tetrahydrooxazolo[5,4-c]pyridine

4-fluorobenzoyl chloride

Phenoxyacetyl chloride

Downstream raw materials:

2-[(3,4-difluorophenoxy)methyl]-5-(4-fluorobenzoyl)-4,5,6,7-tetrahydro-oxazolo[5,4-c]pyridine

5-(4-fluorobenzoyl)-2-[(4-fluorophenoxy)methyl]-4,5,6,7-tetrahydro-oxazolo[5,4-c]pyridine

5-(4-fluorobenzoyl)-2-[(3-fluorophenoxy)methyl]-4,5,6,7-tetrahydro-oxazolo[5,4-c]pyridine

5-(4-fluorobenzoyl)-2-[(2-fluorophenoxy)methyl]-4,5,6,7-tetrahydro-oxazolo[5,4-c]pyridine