NSI-189

Base Information

• Chemical Name: NSI-189
• CAS No.: 1270138-40-3
• Molecular Formula: C22H30N4O
• Molecular Weight: 366.4998
• Mol file: 1270138-40-3.mol

Synonyms:NSI-189;[2-[(3-Methylbutyl)amino]-3-pyridinyl][4-(phenylmethyl)-1-piperazinyl]methanone;[2-[(3-Methylbutyl)amino]-3-pyridinyl][4-(phenylmethyl)-1-piperazinyl]methanone NSI189;NSI-189 [2-[(3-Methylbutyl)amino]-3-pyridinyl][4-(phenylmethyl)-1-piperazinyl]methanone;NSI-189, >=98%;(4-benzylpiperazin-1-yl)-[2-(3-methylbutylamino)pyridin-3-yl]

Chemical Property of NSI-189

Chemical Property:

• Boiling Point: 534.7±50.0 °C(Predicted)
• PKA: 6.18±0.10(Predicted)
• PSA: 48.47000
• Density: 1.134±0.06 g/cm3(Predicted)
• LogP: 3.44640

Purity/Quality:

99% ^*data from raw suppliers

NIS-?189 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: NSI-189 is an investigational drug being developed by Neuralstem Inc., a biopharmaceutical company. NSI-189 is a small molecule in clinical development for major depressive disorder (MDD) and in preclinical development for Angelman syndrome, irradiation-induced cognitive impairment, Type 1 and Type 2 diabetes, and stroke. NSI-189 was studied in phase I and II clinical trials for the treatment of major depressive disorder. As of July 2017, NSI-189 has failed to meet effectiveness outcomes for depression in phase II trials.
• Uses: NSI-189 is an experimental, potential antidepressant, for the treatment for major depressive disorder (MDD), as well as for cognitive impairment and neurodegeneration.

Technology Process of NSI-189

There total 9 articles about NSI-189 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: 75.0%

C30H38N4O2 → (4-benzylpiperazin-1-yl)-[2-(3-methyl-butylamino)pyridin-3-yl] methanone (1270138-40-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h; Reflux;

Reference yield:

C17H18ClN3O (544428-67-3) + 1-amino-3-methylbutane (107-85-7) → (4-benzylpiperazin-1-yl)-[2-(3-methyl-butylamino)pyridin-3-yl] methanone (1270138-40-3)

Guidance literature:

In acetonitrile; at 85 ℃; for 19h; Temperature;

Reference yield:

2-chloronicotinic acid (2942-59-8) → (4-benzylpiperazin-1-yl)-[2-(3-methyl-butylamino)pyridin-3-yl] methanone (1270138-40-3)

Guidance literature:

Multi-step reaction with 5 steps

1: thionyl chloride; N,N-dimethyl-formamide / 3.08 h / 65 °C

2: triethylamine / isopropyl alcohol / 1 h / 20 - 35 °C

3: hydrogenchloride / isopropyl alcohol / 9 h / 50 °C

4: triethylamine / acetonitrile / 3.5 h / 50 °C

5: acetonitrile / 19 h / 85 °C

With hydrogenchloride; thionyl chloride; triethylamine; N,N-dimethyl-formamide; In isopropyl alcohol; acetonitrile;

upstream raw materials:

2-Chloronicotinoyl chloride

1-(2-chloronicotinoyl)-4-tert-butoxycarbonylpiperazine

C₁₇H₁₈ClN₃O

1-amino-3-methylbutane

Refernces

• 1、 -. "Synthesis of a neurostimulative piperazine". . . Retrieved 2016/03/26.