5-amino-1H-imidazo[4,5-b]pyridine-6-carbonitrile

Base Information

• Chemical Name: 5-amino-1H-imidazo[4,5-b]pyridine-6-carbonitrile
• CAS No.: 50738-98-2
• Molecular Formula: C7H5N5
• Molecular Weight: 159.15
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00441333
• Wikidata: Q82258082
• Mol file: 50738-98-2.mol

Synonyms:50738-98-2;5-amino-1H-imidazo[4,5-b]pyridine-6-carbonitrile;SCHEMBL1081479;SCHEMBL12898075;DTXSID00441333;1h-imidazo[4,5-b]pyridine-6-carbonitrile,5-amino-

Chemical Property of 5-amino-1H-imidazo[4,5-b]pyridine-6-carbonitrile

Chemical Property:

• PSA: 92.11000
• LogP: 0.34188
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 159.05449518
• Heavy Atom Count: 12
• Complexity: 219

Purity/Quality:

5-amino-3H-Imidazo[4,5-b]pyridine-6-carbonitrile 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=NC2=C1NC=N2)N)C#N

Technology Process of 5-amino-1H-imidazo[4,5-b]pyridine-6-carbonitrile

There total 1 articles about 5-amino-1H-imidazo[4,5-b]pyridine-6-carbonitrile 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: 90.0%

purine (120-73-0) + malononitrile (109-77-3) → 5-aminoimidazo<4,5-b>pyrimidine-6-carbonitrile (50738-98-2)

Guidance literature:

In isopropyl alcohol; for 66h; Heating;

DOI:10.1002/jhet.5570330218

Reference yield: 22.0%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 5-aminoimidazo<4,5-b>pyrimidine-6-carbonitrile (50738-98-2) → 5-amino-6-cyano-3-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-ribofuranosyl)imidazo[4,5-b]pyridine + C28H25N5O5

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 55 ℃; for 2h; Inert atmosphere;

DOI:10.3998/ark.5550190.p010.075

Reference yield:

5-aminoimidazo<4,5-b>pyrimidine-6-carbonitrile (50738-98-2) → (S)-8-benzoylamino-3-[2,3-bis(tert-butyldimethylsilyloxy)propyl]imidazo[4',5':5,6]pyrido[2,3-d]pyrimidine (1187577-42-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 70 h / 60 °C

2.1: 54 h / 100 °C

2.2: 18 h / 110 °C

3.1: acetic acid / 9 h / 60 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C

5.1: pyridine / 10 h / 20 °C

With pyridine; 1H-imidazole; potassium carbonate; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.11.045

upstream raw materials:

purine

malononitrile

Downstream raw materials:

(S)-8-benzoylamino-3-[2,3-bis(tert-butyldimethylsilyloxy)propyl]imidazo[4',5':5,6]pyrido[2,3-d]pyrimidine

(S)-8-benzoylamino-3-[2,3-dihydroxypropyl]imidazo[4',5':5,6]pyrido[2,3-d]pyrimidine

(S)-8-benzoylamino-3-[3-(4,4'-dimethoxytrityloxy)-2-hydroxypropyl]imidazo[4',5':5,6]pyrido[2,3-d]pyrimidine

8-benzoylamino-3-[(2S)-3-(4,4'-dimethoxytrityloxy)-2-[[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]oxy]-propyl]imidazo[4',5':5,6]pyrido[2,3-d]pyrimidine