3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

Base Information

• Chemical Name: 3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one
• CAS No.: 21991-39-9
• Molecular Formula: C7H7N3O
• Molecular Weight: 149.15000
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40358714
• Wikidata: Q82139504
• Mol file: 21991-39-9.mol

Synonyms:3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one;21991-39-9;3-methyl-1H-imidazo[4,5-b]pyridin-2-one;3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one;2H-Imidazo[4,5-b]pyridin-2-one, 1,3-dihydro-3-methyl-;Oprea1_803736;3-methylimidazopyridin-2-one;SCHEMBL1503016;SCHEMBL14035127;DTXSID40358714;UNTZTFGDFVDERP-UHFFFAOYSA-N;WAA99139;MFCD01081498;STL577155;AKOS016006902;AC-27233;DS-16012;CS-0112221;C74108;F1907-1676;Z1255427740

Chemical Property of 3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

Chemical Property:

• Melting Point: 233-235 °C
• PKA: 12.47±0.20(Predicted)
• PSA: 50.94000
• Density: 1.293±0.06 g/cm3(Predicted)
• LogP: 0.67390
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.058911855
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

97% ^*data from raw suppliers

3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C=CC=N2)NC1=O
• Uses: 3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one is used as a reactant in the molecular design, synthesis and hypoglycemic activity of a series of thiazolidinediones in relation to improvement of insulin resistance and cardiac hypertrophy and bioavailability.

Technology Process of 3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

There total 11 articles about 3-Methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one 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: 93.0%

1-acetyl-3-methyl-1,3-dihydro-2H-imidazo<4,5-b>pyridin-2-one (103409-31-0) → 3-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (21991-39-9)

Guidance literature:

With sodium hydroxide; In water; at 70 ℃; for 0.333333h;

DOI:10.1002/jhet.5570220427

Reference yield: 70.0%

3-amino-2-methylaminopyridine (5028-20-6) + 1,1'-carbonyldiimidazole (530-62-1) → 3-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (21991-39-9)

Guidance literature:

In tetrahydrofuran; at 23 ℃; for 15h; Inert atmosphere;

DOI:10.1016/j.bmcl.2014.12.089

Reference yield:

2-Chloro-3-nitropyridine (5470-18-8,34515-82-7) → 3-methyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (21991-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 80 °C

2: hydrogen / palladium 10% on activated carbon / ethanol / 20 °C

3: tetrahydrofuran / 5 h / Reflux

With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; ethanol;

upstream raw materials:

1-acetyl-3-methyl-1,3-dihydro-2H-imidazo<4,5-b>pyridin-2-one

1-t-butoxycarbonyl-3-methyl-1,3-dihydro-2H-imidazo<4,5-b>pyridin-2-one

3-amino-2-methylaminopyridine

1,1'-carbonyldiimidazole

Downstream raw materials:

2-chloro-3-methyl-3H-imidazo[4,5-b]pyridine

3-methyl-3H-imidazo[4,5-b]pyridin-2-amine