3-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-(4-methoxybenzyl)acrylamide

Base Information

• Chemical Name: 3-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-(4-methoxybenzyl)acrylamide
• CAS No.: 185259-85-2
• Molecular Formula: C₂₃H₂₇N₃O₂
• Molecular Weight: 377.486
• European Community (EC) Number: 633-752-9
• Wikidata: Q76323634
• Pharos Ligand ID: NPNZ24WLU6K1
• ChEMBL ID: CHEMBL344127
• Mol file: 185259-85-2.mol

Synonyms:3-(3-(2-dimethylaminoethyl)-H-indol-5-yl)-N-(4-methoxybenzyl)acrylamide;GR 46611;GR46611

Chemical Property of 3-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-(4-methoxybenzyl)acrylamide

Chemical Property:

• Vapor Pressure: 1.43E-16mmHg at 25°C
• Boiling Point: 645.9°Cat760mmHg
• Flash Point: 344.4°C
• PSA: 57.36000
• Density: 1.168g/cm³
• LogP: 4.00110
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 28 mg/mL, soluble
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 377.21032711
• Heavy Atom Count: 28
• Complexity: 514

Purity/Quality:

99%min ^*data from raw suppliers

GR46611 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC1=CNC2=C1C=C(C=C2)C=CC(=O)NCC3=CC=C(C=C3)OC
• Isomeric SMILES: CN(C)CCC1=CNC2=C1C=C(C=C2)/C=C/C(=O)NCC3=CC=C(C=C3)OC
• Uses: GR 46611is a 5-HT1D agonist.

Technology Process of 3-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-(4-methoxybenzyl)acrylamide

There total 4 articles about 3-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-(4-methoxybenzyl)acrylamide 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: 44.0%

N-(4-methoxybenzyl)-acrylamide (70875-53-5) + 3-(dimethylaminoethyl)-5-[(trifluoromethanesulfonyl)oxy]indole → GR 46611 (185259-85-2)

Guidance literature:

With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine; In N,N-dimethyl-formamide; at 85 ℃; for 18h;

DOI:10.1021/jm9604890

Reference yield:

N-(4-methoxybenzyl)-acrylamide (70875-53-5) + 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (17274-65-6) → GR 46611 (185259-85-2)

Guidance literature:

With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In N,N-dimethyl-formamide; at 100 ℃; for 3h;

Reference yield:

bufotenin (487-93-4) → GR 46611 (185259-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 mg / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

2: 44 percent / Pd(OAc)2, 1,3-bis(diphenylphosphino)propane, Et₃N / dimethylformamide / 18 h / 85 °C

With palladium diacetate; 1,3-bis-(diphenylphosphino)propane; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm9604890

upstream raw materials:

N-(4-methoxybenzyl)-acrylamide

bufotenin

4-methoxy-benzylamine

5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Refernces

• 1、 Barf,De Boer,Wikstrom,Peroutka,Svensson,Ennis,Ghazal,McGuire,Smith. "5-HT(1D) receptor agonist properties of novel 2-[5- [[(trifluoromethyl)sulfonyl]oxy]indolyl]ethylamines and their use as synthetic intermediates". . p. 4717 - 4726. Retrieved 2007/10/03.