Cabergolinic acid methyl ester

Base Information

• Chemical Name: Cabergolinic acid methyl ester
• CAS No.: 72821-79-5
• Molecular Formula: C19H22 N2 O2
• Molecular Weight: 310.396
• Hs Code.: 2933990090
• European Community (EC) Number: 805-968-5
• Nikkaji Number: J1.808.220I
• Wikidata: Q76416749
• Mol file: 72821-79-5.mol

Synonyms:72821-79-5;Cabergolinic acid methyl ester;SCHEMBL1888524;AKOS015961776;AC-14871

Chemical Property of Cabergolinic acid methyl ester

Chemical Property:

• Vapor Pressure: 3.73E-09mmHg at 25°C
• Refractive Index: 1.613
• Boiling Point: 474.1°C at 760 mmHg
• PKA: 17.52±0.40(Predicted)
• Flash Point: 240.5°C
• PSA: 45.33000
• Density: 1.19g/cm³
• LogP: 2.79500
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 310.168127949
• Heavy Atom Count: 23
• Complexity: 480

Purity/Quality:

99%, ^*data from raw suppliers

6-Allyl-8β-carboxyergolineMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC2C(CC3=CNC4=CC=CC2=C34)N(C1)CC=C
• Isomeric SMILES: COC(=O)[C@@H]1C[C@H]2[C@@H](CC3=CNC4=CC=CC2=C34)N(C1)CC=C

Technology Process of Cabergolinic acid methyl ester

There total 8 articles about Cabergolinic acid methyl ester 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: 96.5%

methanol (67-56-1) + N-<<<3-(dimethylamino)propyl>amino>carbonyl>-N-ethyl-6-(2-propenyl)-ergoline-8β-carboxamide (81409-91-8) → methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (72821-79-5)

Guidance literature:

With triethylamine; at 20 ℃; Product distribution / selectivity;

Reference yield: 94.0%

methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (30341-92-5) + allyl bromide (106-95-6) → methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (72821-79-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 35 ℃; for 2.5h;

DOI:10.1039/c3ra43417f

Reference yield:

methyl ergoline-8β-carboxylate hydrochloride (1075250-77-9) + allyl bromide (106-95-6) → methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (72821-79-5)

Guidance literature:

With triethylamine; In N,N-dimethylformide; at 20 - 30 ℃; for 4 - 5h; Product distribution / selectivity;

upstream raw materials:

methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

allyl bromide

methyl ergoline-8β-carboxylate hydrochloride

methanol

Downstream raw materials:

(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid

(6aR,9R,10aR)-7-allyl-N⁹-[3-(dimethylamino)propyl]-N⁴-ethyl-N⁹-(ethylcarbamoyl)-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide

N-<3-(dimethylamino)propyl>-N-<(phenylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide

N-<3-(dimethylamino)propyl>-N-<(methylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide

Refernces

• 1、 Dosa, Peter I.,Ward, Tim,Walters, Michael A.,Kim, Suck Won. "Synthesis of novel analogs of cabergoline: Improving cardiovascular safety by removing 5-HT2B receptor agonism". . p. 254 - 258. Retrieved 2013/04/10.
• 2、 Benes, Jan,Cerny, Antonin,Miller, Vladimir,Kudrnac, Stanislav. "EPIMERIZATION OF ESTERS OF STEREOISOMERIC 8-ERGOLINECARBOXYLIC ACIDS ON CARBON C(8)". . p. 1333 - 1340. Retrieved 2007/10/02.