N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide

Base Information

• Chemical Name: N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide
• CAS No.: 342417-04-3
• Molecular Formula: C17H19ClN2O
• Molecular Weight: 302.804
• Mol file: 342417-04-3.mol

Synonyms:NETUPITANT IST-2;N-?(tert-?Butyl)?-?6-?chloro-?4-?(2-?methylphenyl)?nicotinamide;3-Pyridinecarboxamide, 6-chloro-N-(1,1-dimethylethyl)-4-(2-methylphenyl)-

Chemical Property of N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide

Chemical Property:

• PSA: 41.99000
• LogP: 4.62960
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99.9% by HPLC ^*data from raw suppliers

N-?(tert-?Butyl)?-?6-?chloro-?4-?(2-?methylphenyl)?nicotinamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-?(tert-?Butyl)?-?6-?chloro-?4-?(2-?methylphenyl)?nicotinamide is a reagent used in the synthesis of NK1/NK3 receptor antagonists used in the treatment of depression.

Technology Process of N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide

There total 4 articles about N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide 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: 88.0%

N-tert-butyl-6-chloro-nicotinamide (115309-58-5) + o-tolyl magnesium chloride (33872-80-9) → N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide (342417-04-3)

Guidance literature:

N-tert-butyl-6-chloro-nicotinamide; o-tolyl magnesium chloride; In tetrahydrofuran; at 0 - 30 ℃; for 21h;

With acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

Reference yield:

N-tert-butyl-6-chloro-nicotinamide (115309-58-5) + tert-butyl methyl ether (1634-04-4) + o-tolyl magnesium chloride (33872-80-9) + 2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2) → N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide (342417-04-3)

Guidance literature:

In tetrahydrofuran; methanol;

Reference yield:

6-Chloronicotinoyl chloride (58757-38-3) → N-tert-butyl-6-chloro-4-(o-tolyl)nicotinamide (342417-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 66.8 g / toluene / 1.17 h

2.1: tetrahydrofuran / 21 h / 20 - 30 °C

2.2: acetic acid / tetrahydrofuran / 0.25 h

2.3: DDQ / tetrahydrofuran / 1 h / 20 °C

In tetrahydrofuran; toluene; 2.1: Grignard addition;

DOI:10.1021/jo0523666

upstream raw materials:

N-tert-butyl-6-chloro-nicotinamide

o-tolyl magnesium chloride

6-Chloronicotinoyl chloride

tert-butyl methyl ether

Downstream raw materials:

[6-(4-methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl]carbamic acid methyl ester

4-(2-methylphenyl)-6-(4-methylpiperazinyl)-3-pyridinecarboxamide

4-(2-methylphenyl)-6-(4-morpholinyl)-3-pyridinecarboxamide

[6-(morpholin-4-yl)-4-(o-tolyl)pyridin-3-yl]carbamic acid methyl ester