(5R,8S,10R)-2-Chloro-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline

Base Information

• Chemical Name: (5R,8S,10R)-2-Chloro-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline
• CAS No.: 162070-36-2
• Molecular Formula: C₁₈H₂₀ClN₅
• Molecular Weight: 341.843
• Mol file: 162070-36-2.mol

Synonyms:2-Chloro-6-methyl-8-alpha-(1H-1,2,4-triazol-1-ylmethyl)ergoline;(5R,8S,10R)-2-Chloro-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline;Ergoline, 2-chloro-6-methyl-8-(1H-1,2,4-triazol-1-ylmethyl)-, (8-alpha)-;162070-36-2;C18-H20-Cl-N5;LS-64397

Chemical Property of (5R,8S,10R)-2-Chloro-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline

Chemical Property:

• Vapor Pressure: 2.55E-13mmHg at 25°C
• Boiling Point: 577.1°Cat760mmHg
• Flash Point: 302.8°C
• Density: 1.52g/cm³
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 341.1407234
• Heavy Atom Count: 24
• Complexity: 476

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CC(CC2C1CC3=C(NC4=CC=CC2=C34)Cl)CN5C=NC=N5
• Isomeric SMILES: CN1C[C@H](CC2[C@H]1CC3=C(NC4=CC=CC2=C34)Cl)CN5C=NC=N5

Technology Process of (5R,8S,10R)-2-Chloro-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline

There total 7 articles about (5R,8S,10R)-2-Chloro-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline 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: 52.0%

1,2,4-Triazole (288-88-0) + Toluene-4-sulfonic acid (6aR,9S,10aR)-5-chloro-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester (162070-44-2) → (5R,8S,10R)-2-chloro-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline (160730-54-1,162070-36-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 90 ℃; for 2h;

DOI:10.1248/cpb.42.2042

Reference yield: 45.0%

(6aR,9S,10aR)-7-Methyl-9-[1,2,4]triazol-1-ylmethyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline (115178-30-8) → (5R,8S,10R)-2-chloro-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline (160730-54-1,162070-36-2)

Guidance literature:

With N-chloro-succinimide; In 1,4-dioxane; at 60 ℃; for 1h;

DOI:10.1248/cpb.42.2042

Reference yield:

methyl (5R,8R,10R)-2-chloro-6-methyl-8-ergolinecarboxylate (110883-13-1) → (6aR,9R,10aR)-5-Chloro-7-methyl-9-[1,2,4]triazol-1-ylmethyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline (162070-36-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / LiAlH₄ / tetrahydrofuran / 0.5 h

2: 84 percent / pyridine / 3 h / Ambient temperature

3: 1.) NaH / 1.) DMF, 2.) DMF, 90 deg C, 2 h

With pyridine; lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran;

DOI:10.1248/cpb.42.1463

upstream raw materials:

1,2,4-Triazole

(5R,8R,10R)-2-chloro-6-methyl-8-ergolinylmethyl p-toluenesulfonate

methyl (5R,8R,10R)-2-chloro-6-methyl-8-ergolinecarboxylate

((6aR,9R,10aR)-5-Chloro-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-yl)-methanol