2(S)-[5-[2-(2-Azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-[2-(4-pyridyl)ethyl]propan-1-amine

Base Information

• Chemical Name: 2(S)-[5-[2-(2-Azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-[2-(4-pyridyl)ethyl]propan-1-amine
• CAS No.: 255863-81-1
• Molecular Formula: C₃₇H₄₆N₄O
• Molecular Weight: 562.798
• Mol file: 255863-81-1.mol

Synonyms:

Chemical Property of 2(S)-[5-[2-(2-Azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-[2-(4-pyridyl)ethyl]propan-1-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(S)-[5-[2-(2-Azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-[2-(4-pyridyl)ethyl]propan-1-amine

There total 18 articles about 2(S)-[5-[2-(2-Azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-[2-(4-pyridyl)ethyl]propan-1-amine 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: 78.0%

N-{(2S)-2-[5-[2-(2-azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]propyl}-4-nitro-N-(2-pyridin-4-ylethyl)benzenesulfonamide → (2S)-2-[5-[2-(2-azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-(2-pyridin-4-ylethyl)propan-1-amine (255863-81-1)

Guidance literature:

With lithium hydroxide; mercaptoacetic acid; In N,N-dimethyl-formamide; at 40 ℃; for 2h;

DOI:10.1016/j.tetasy.2003.08.038

Reference yield: 70.0%

4-vinylpyridine (100-43-6,329041-72-7) + (2S)-2-[5-[2-(2-azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]propan-1-amine → (2S)-2-[5-[2-(2-azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-(2-pyridin-4-ylethyl)propan-1-amine (255863-81-1)

Guidance literature:

With acetic acid; In toluene; at 80 ℃; for 2h;

DOI:10.1016/j.tetasy.2003.08.038

Reference yield:

(S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester (217192-27-3) → (2S)-2-[5-[2-(2-azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-(2-pyridin-4-ylethyl)propan-1-amine (255863-81-1)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. K₂CO₃ / tetrahydrofuran

2: aq. KOH / methanol / Heating

3: PyBOP; Et₃N / CH₂Cl₂

4: TFA; anisole / CH₂Cl₂

5: satd. aq. NaHCO₃ / CH₂Cl₂

6: Ph₃P; DEAD / benzene

7: PrNH₂

With propylamine; potassium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydrogencarbonate; potassium carbonate; methoxybenzene; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; benzene; 5: Schotten-Baumann reaction;

DOI:10.1016/S0960-894X(01)00512-1

upstream raw materials:

isoquinuclidine

4-(2-hydroxyethyl)pyridine

2-(pyridine-4-yl)acetic acid hydrochloride

(S)-2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester