N-(1-azabicyclo[2.2.2]oct-3-yl)-6-bromo-7-nitro-1H-benzimidazole-4-carboxamide

Base Information

• Chemical Name: N-(1-azabicyclo[2.2.2]oct-3-yl)-6-bromo-7-nitro-1H-benzimidazole-4-carboxamide
• CAS No.: 255064-05-2
• Molecular Formula: C₁₅H₁₆BrN₅O₃
• Molecular Weight: 394.228
• Mol file: 255064-05-2.mol

Synonyms:6-bromo-7-nitro-1H-benzoimidazole-4-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide

Chemical Property of N-(1-azabicyclo[2.2.2]oct-3-yl)-6-bromo-7-nitro-1H-benzimidazole-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(1-azabicyclo[2.2.2]oct-3-yl)-6-bromo-7-nitro-1H-benzimidazole-4-carboxamide

There total 5 articles about N-(1-azabicyclo[2.2.2]oct-3-yl)-6-bromo-7-nitro-1H-benzimidazole-4-carboxamide 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-bromo-3-methylbenzene-1,2-diamine (76153-06-5) → 6-bromo-7-nitro-1H-benzoimidazole-4-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide (255064-05-2)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂O / 5 h / 100 °C

2: HNO₃; H₂SO₄ / 2 h / 5 °C

3: KMnO₄; 0.5 N NaOH / 5 h / 100 °C

4: dimethylformamide / 1 h / 40 °C

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 24 h / 50 °C

With sodium hydroxide; potassium permanganate; sulfuric acid; nitric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; N,N-dimethyl-formamide; 1: Condensation / 2: Nitration / 3: Oxidation / 4: Condensation / 5: Acylation;

DOI:10.1021/jm991076c

Reference yield:

quinuclidin-3-amine (76883-48-2,120570-05-0,123536-15-2,6238-14-8,781591-76-2) + (6-bromo-7-nitro-1H-benzoimidazol-4-yl)-imidazol-1-yl-methanone → 6-bromo-7-nitro-1H-benzoimidazole-4-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide (255064-05-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 50 ℃; for 24h;

DOI:10.1021/jm991076c

Reference yield:

6-bromo-4-methyl-1H-benzo[d]imidazole (255064-10-9) → 6-bromo-7-nitro-1H-benzoimidazole-4-carboxylic acid (1-aza-bicyclo[2.2.2]oct-3-yl)-amide (255064-05-2)

Guidance literature:

Multi-step reaction with 4 steps

1: HNO₃; H₂SO₄ / 2 h / 5 °C

2: KMnO₄; 0.5 N NaOH / 5 h / 100 °C

3: dimethylformamide / 1 h / 40 °C

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 24 h / 50 °C

With sodium hydroxide; potassium permanganate; sulfuric acid; nitric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; 1: Nitration / 2: Oxidation / 3: Condensation / 4: Acylation;

DOI:10.1021/jm991076c

upstream raw materials:

quinuclidin-3-amine

5-bromo-3-methylbenzene-1,2-diamine

6-bromo-4-methyl-1H-benzo[d]imidazole

6-bromo-4-methyl-7-nitro-1H-benzoimidazole