methyl 5-(tert-butoxycarbonyl(methyl)amino)-2-chloroisonicotinate

Base Information

• Chemical Name: methyl 5-(tert-butoxycarbonyl(methyl)amino)-2-chloroisonicotinate
• CAS No.: 1034131-89-9
• Molecular Formula: C₁₃H₁₇ClN₂O₄
• Molecular Weight: 300.742
• Mol file: 1034131-89-9.mol

Synonyms:

Chemical Property of methyl 5-(tert-butoxycarbonyl(methyl)amino)-2-chloroisonicotinate

Chemical Property:

• Boiling Point: 407.9±45.0 °C(Predicted)
• Density: 1.252±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Methyl5-((tert-Butoxycarbonyl)(methyl)amino)-2-chloroisonicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Methyl 5-((tert-Butoxycarbonyl)(methyl)amino)-2-chloroisonicotinate is used as a reactant in the preparation of 1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one derivatives as FAAH inhibitors.

Technology Process of methyl 5-(tert-butoxycarbonyl(methyl)amino)-2-chloroisonicotinate

There total 4 articles about methyl 5-(tert-butoxycarbonyl(methyl)amino)-2-chloroisonicotinate 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:

5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid (171178-46-4) + methyl iodide (74-88-4) → methyl 5-(tert-butoxycarbonyl(methyl)amino)-2-chloroisonicotinate (1034131-89-9)

Guidance literature:

5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

Reference yield:

2-chloro-5-nitropyridine (4548-45-2) → methyl 5-(tert-butoxycarbonyl(methyl)amino)-2-chloroisonicotinate (1034131-89-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrogen / nickel / ethanol / 5 h / 20 °C / 2327.23 Torr

2.1: 1,4-dioxane / 20 °C / Heating / reflux

3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / hexanes; diethyl ether / 2 h / -78 - -15 °C

3.2: -78 - 20 °C

3.3: 20 °C / pH 3

4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

4.2: 1 h / 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; hydrogen; sodium hydride; nickel; In 1,4-dioxane; hexanes; diethyl ether; ethanol; N,N-dimethyl-formamide;

Reference yield:

6-Chloro-pyridin-3-ylamine (5350-93-6) → methyl 5-(tert-butoxycarbonyl(methyl)amino)-2-chloroisonicotinate (1034131-89-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,4-dioxane / 20 °C / Heating / reflux

2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / hexanes; diethyl ether / 2 h / -78 - -15 °C

2.2: -78 - 20 °C

2.3: 20 °C / pH 3

3.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

3.2: 1 h / 20 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydride; In 1,4-dioxane; hexanes; diethyl ether; N,N-dimethyl-formamide;

upstream raw materials:

5-[N-(tert-butoxycarbonyl)amino]-2-chloropyridine-4-carboxylic acid

methyl iodide

6-Chloro-pyridin-3-ylamine

2-chloro-5-nitropyridine

Downstream raw materials:

methyl 2-chloro-5-(methylamino)isonicotinate

2-chloro-5-(methylamino)isonicotinic acid

Refernces

• 1、 -. "QUINOLONES AND AZAQUINOLONES THAT INHIBIT PROLYL HYDROXYLASE". Page/Page column 58. . Retrieved 2008/12/08.