(10-Methoxy-1,6-dimethylergolin-8-yl)methyl 5-bromopyridine-3-carboxylate

Base Information

• Chemical Name: (10-Methoxy-1,6-dimethylergolin-8-yl)methyl 5-bromopyridine-3-carboxylate
• CAS No.: 27848-84-6
• Molecular Formula: C24H26BrN3O3
• Molecular Weight: 484.393
• Hs Code.: 29396100
• NSC Number: 150531
• DSSTox Substance ID: DTXSID00860404
• Wikidata: Q27167040
• ChEMBL ID: CHEMBL4744096
• Mol file: 27848-84-6.mol

Synonyms:(10-methoxy-1,6-dimethylergolin-8-yl)methyl 5-bromopyridine-3-carboxylate;Nargoline;Oprea1_110366;CHEMBL4744096;CHEBI:95219;DTXSID00860404;YSEXMKHXIOCEJA-UHFFFAOYSA-N;HMS3266B07;NSC150531;STL445693;AKOS040894269;L000717;BRD-A99721021-001-01-3;Q27167040;Ergoline-8.beta.-methanol,6-dimethyl-, 5-bromonicotinate (ester);10-Methoxy-1,6-dimethylergoline-8.beta.-methanol 5-bromonicotinate ester;Ergoline-8-methanol,6-dimethyl-, (8.beta.)-, 5-bromo-3-pyridinecarboxylate ester;Ergoline-8-methanol,6-dimethyl-, 5-bromo-3-pyridinecarboxylate (ester), (8.beta.)-;5-bromo-3-pyridinecarboxylic acid (10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6H-indolo[4,3-fg]quinoline-9-yl)methyl ester

Chemical Property of (10-Methoxy-1,6-dimethylergolin-8-yl)methyl 5-bromopyridine-3-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 136-138°
• Refractive Index: 1.6200 (estimate)
• Boiling Point: 594.4 °C at 760 mmHg
• PKA: 6.33±0.40(Predicted)
• Flash Point: 313.3 °C
• PSA: 56.59000
• Density: 1.47 g/cm³
• LogP: 3.84880
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, freely soluble in methylene chloride, soluble in ethanol (96 per cent).
• Water Solubility.: Soluble in alcohol, chloroform, and acetone. Insoluble in water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 483.11575
• Heavy Atom Count: 31
• Complexity: 681

Purity/Quality:

99% ^*data from raw suppliers

Nicergoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CC(CC2(C1CC3=CN(C4=CC=CC2=C34)C)OC)COC(=O)C5=CC(=CN=C5)Br
• Uses: antipsychotic Nicergoline is a drug used for age-dependent cognitive impairment such as Alzheimers disease and other types of dementia. Nicergoline has shown to protect cultured neurons against β-amyloid toxicity. Nicergoline protects against neuronal cell death induced by activated microglia and astrocytes through the inhibition of inflammatory mediators and the upregulation of neurotrophic factors by glial cells. Nicergoline is a drug used for age-dependent cognitive impairment and it protects cultured neurons against β-amyloid toxicity.
• Therapeutic Function: Vasodilator

Technology Process of (10-Methoxy-1,6-dimethylergolin-8-yl)methyl 5-bromopyridine-3-carboxylate

There total 16 articles about (10-Methoxy-1,6-dimethylergolin-8-yl)methyl 5-bromopyridine-3-carboxylate 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: 92.0%

C21H22BrN3O3 + methyl iodide (74-88-4) → Nicergoline (27848-84-6)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; at -5 ℃; for 3h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 91.2%

5-bromonicotinoyl chloride (39620-02-5) + 1-Methyl-10alpha-methoxy-9,10-dihydrolysergol (35155-28-3) → nicergoline (27848-84-6,28057-46-7,58001-19-7,58001-20-0,58001-21-1,140387-88-8)

Guidance literature:

With triethylamine; In chloroform; at 20 - 30 ℃; for 2h;

Reference yield:

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + 1-Methyl-10alpha-methoxy-9,10-dihydrolysergol (35155-28-3) → nicergoline (27848-84-6,28057-46-7,58001-19-7,58001-20-0,58001-21-1,140387-88-8)

Guidance literature:

5-bromo-3-pyridinecarboxylic acid; With oxalyl dichloride; In dichloromethane; at 20 ℃; for 3h;

1-Methyl-10alpha-methoxy-9,10-dihydrolysergol; With triethylamine; In dichloromethane; at 20 ℃; Reagent/catalyst;

upstream raw materials:

5-bromonicotinoyl chloride

1-Methyl-10alpha-methoxy-9,10-dihydrolysergol

lysergol

5-bromo-3-pyridinecarboxylic acid

Downstream raw materials:

5-bromo-3-pyridinecarboxylic acid

1-Methyl-10alpha-methoxy-9,10-dihydrolysergol

Refernces

• 1、 -. "Synthesis method and application of nicergoline". Paragraph 0029; 0034; 0037-0038; 0041; 0042-0047. . Retrieved 2021/10/27.
• 2、 -. "Novel preparation method of nicergoline". . . Retrieved 2020/04/22.