(3-(2-(Dimethylamino)ethyl)-2-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-1H-indol-5-yl)-N-methylmethanesulfonamide

Base Information

• Chemical Name: (3-(2-(Dimethylamino)ethyl)-2-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-1H-indol-5-yl)-N-methylmethanesulfonamide
• CAS No.: 545338-89-4
• Molecular Formula: C₂₇H₃₇N₅O₂S
• Molecular Weight: 495.689
• European Community (EC) Number: 839-367-4
• UNII: TG89P1S80G
• Wikidata: Q27289955
• Mol file: 545338-89-4.mol

Synonyms:545338-89-4;UNII-TG89P1S80G;Sumatriptan succinate specified impurity A [EP];TG89P1S80G;(3-(2-(Dimethylamino)ethyl)-2-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-1H-indol-5-yl)-N-methylmethanesulfonamide;2-[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl] Sumatriptan;1-[3-[2-(dimethylamino)ethyl]-2-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1H-indol-5-yl]-N-methylmethanesulfonamide;1H-Indole-5-methanesulfonamide, 3-(2-(dimethylamino)ethyl)-2-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-N-methyl-;[3-[2-(diMethylaMino)ethyl]-2-[[3-[2-(diMethylaMino)ethyl]-1H-indol-5-yl]Methyl]-1H-indol-5-yl]-N-MethylMethanesulfonaMide, succinate salt;SCHEMBL946435;Q27289955;SUMATRIPTAN SUCCINATE IMPURITY A [EP IMPURITY]

Chemical Property of (3-(2-(Dimethylamino)ethyl)-2-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-1H-indol-5-yl)-N-methylmethanesulfonamide

Chemical Property:

• PSA: 92.61000
• LogP: 4.96910
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 495.26679661
• Heavy Atom Count: 35
• Complexity: 770

Purity/Quality:

98% ^*data from raw suppliers

2-[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl]Sumatriptan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNS(=O)(=O)CC1=CC2=C(C=C1)NC(=C2CCN(C)C)CC3=CC4=C(C=C3)NC=C4CCN(C)C
• Uses: 2-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl] Sumatriptan Succinate is an impurity of Sumatriptan (S810000), a serotonin 5HT-1-receptor agonist. 2-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl] Sumatriptan Succinate (Sumatriptan EP Impurity A) is an impurity of Sumatriptan (S810000), a serotonin 5HT-1-receptor agonist.

Technology Process of (3-(2-(Dimethylamino)ethyl)-2-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-1H-indol-5-yl)-N-methylmethanesulfonamide

There total 5 articles about (3-(2-(Dimethylamino)ethyl)-2-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-1H-indol-5-yl)-N-methylmethanesulfonamide 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: 26.0%

sumatripan (103628-46-2) + 3-[2-(dimethylamino)ethyl]-5-indolemethanol (334981-08-7) → [[3-[2-(dimethylamino)ethyl]-2-[[3-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1H-indol-5-yl]-N-methylmethanesulfonamide (545338-89-4)

Guidance literature:

In propionic acid; for 3h; Heating;

Reference yield:

ethyl 3-[2-(dimethylamino)ethyl]-5-indolecarboxylate (137499-21-9) → [[3-[2-(dimethylamino)ethyl]-2-[[3-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1H-indol-5-yl]-N-methylmethanesulfonamide (545338-89-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

2: 26 percent / propionic acid / 3 h / Heating

With lithium aluminium tetrahydride; In tetrahydrofuran; propionic acid; 2: Friedel-Crafts reaction;

Reference yield:

p-aminoethylbenzoate (94-09-7) → [[3-[2-(dimethylamino)ethyl]-2-[[3-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1H-indol-5-yl]-N-methylmethanesulfonamide (545338-89-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaNO₂*H₂O; aq. HCl / -10 °C

1.2: SnCl₂*2H₂O; aq. HCl

2.1: 34 percent / H₂SO₄ conc. / toluene / 6 h / Heating

3.1: 77 percent / ethanol; H₂O / 6 h / 50 °C

4.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

5.1: 26 percent / propionic acid / 3 h / Heating

With hydrogenchloride; lithium aluminium tetrahydride; sulfuric acid; sodium nitrite; In tetrahydrofuran; ethanol; water; propionic acid; toluene; 2.1: Fisher reaction / 5.1: Friedel-Crafts reaction;

upstream raw materials:

sumatripan

3-[2-(dimethylamino)ethyl]-5-indolemethanol

ethyl 3-[2-(dimethylamino)ethyl]-5-indolecarboxylate

p-aminoethylbenzoate

Refernces