2-Chloro-5-methyl-1,6-naphthyridine

Base Information

• Chemical Name: 2-Chloro-5-methyl-1,6-naphthyridine
• CAS No.: 140692-93-9
• Molecular Formula: C9H7 Cl N2
• Molecular Weight: 178.62
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20391841
• Wikidata: Q82189574
• ChEMBL ID: CHEMBL344086
• Mol file: 140692-93-9.mol

Synonyms:2-chloro-5-methyl-1,6-naphthyridine;140692-93-9;2-chloro-5-methyl[1,6]naphthyridine;CHEMBL344086;SCHEMBL1037540;DTXSID20391841;MFCD01443634;AKOS005070250;1,6-Naphthyridine, 2-chloro-5-methyl-;2-chloro-5-methyl-[1,6]-naphthyridine;CS-0318542;3N-041;E77941;A910987;J-508859

Chemical Property of 2-Chloro-5-methyl-1,6-naphthyridine

Chemical Property:

• Melting Point: 96～98℃
• PSA: 25.78000
• LogP: 2.59160
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 178.0297759
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99%min ^*data from raw suppliers

2-Chloro-5-methyl[1,6]naphthyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC=CC2=C1C=CC(=N2)Cl

Technology Process of 2-Chloro-5-methyl-1,6-naphthyridine

There total 4 articles about 2-Chloro-5-methyl-1,6-naphthyridine 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: 77.0%

medorinone (88296-61-1) → 2-chloro-5-methyl-1,6-naphthyridine (140692-93-9)

Guidance literature:

With phosphorus pentachloride; trichlorophosphate; for 7h; Heating;

DOI:10.1021/jm00104a012

Reference yield:

4-amino-3-penten-2-one (1118-66-7) → 2-chloro-5-methyl-1,6-naphthyridine (140692-93-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,N-dimethyl-formamide / 27.75 h / 20 °C / Heating / reflux

2.1: 1,4-dioxane / 2.5 h / Heating / reflux

3.1: ammonium acetate / N,N-dimethyl-formamide / 2 h / Heating / reflux

4.1: phosphorus pentachloride; trichlorophosphate / 7 h / Heating / reflux

4.2: 0 - 10 °C

With phosphorus pentachloride; ammonium acetate; trichlorophosphate; In 1,4-dioxane; N,N-dimethyl-formamide;

Reference yield:

5-acetyl-6-methyl-2(1H)-pyridinone (5220-65-5) → 2-chloro-5-methyl-1,6-naphthyridine (140692-93-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,4-dioxane / 2.5 h / Heating / reflux

2.1: ammonium acetate / N,N-dimethyl-formamide / 2 h / Heating / reflux

3.1: phosphorus pentachloride; trichlorophosphate / 7 h / Heating / reflux

3.2: 0 - 10 °C

With phosphorus pentachloride; ammonium acetate; trichlorophosphate; In 1,4-dioxane; N,N-dimethyl-formamide;

upstream raw materials:

medorinone

4-amino-3-penten-2-one

5-acetyl-6-methyl-2(1H)-pyridinone

5-Acetyl-6-((E)-2-dimethylamino-vinyl)-1H-pyridin-2-one

Downstream raw materials:

[2-(4-benzylpiperidin-1-yl)ethyl]-(5-methyl[1,6]naphthyridin-2-yl)amine

2-(4-benzylpiperidin-1-yl)-N-(5-methyl[1,6]naphthyridin-2-yl)acetamide

1-[2-(4-benzylpiperidin-1-yl)ethyl]-3-(5-methyl[1,6]naphthyridin-2-yl)urea

Refernces

• 1、 Singh, Baldev,Lesher, George Y.,Pluncket, Kevin C.,Pagani, Edward D.,Bode, Donald C.,et al.. "Novel cAMP PDE III Inhibitors: 1,6-Naphthyridin-2(1H)-ones". . p. 4858 - 4865. Retrieved 2007/10/02.