4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-(3-aminophenyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol

Base Information

• Chemical Name: 4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-(3-aminophenyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol
• CAS No.: 913640-04-7
• Molecular Formula: C₂₁H₂₁N₇O₂
• Molecular Weight: 403.443
• Mol file: 913640-04-7.mol

Synonyms:4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-(3-aminophenyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol

Chemical Property of 4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-(3-aminophenyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-(3-aminophenyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol

There total 16 articles about 4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-(3-aminophenyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol 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: 75.0%

4-[6-(3-aminophenyl)-4-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl]-1,2,5-oxadiazol-3-amine + 2-methyl-but-3-yn-2-ol (115-19-5) → 4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-(3-aminophenyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol (913640-04-7)

Guidance literature:

With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

Reference yield: 62.0%

4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol (913642-19-0) + 3-Aminophenylboronic acid (30418-59-8,280563-63-5) → 4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-(3-aminophenyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol (913640-04-7)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 70 ℃; for 12h; Product distribution / selectivity;

Reference yield:

2-chloro-N-ethyl-5-nitro-4-pyridinamine (607373-89-7) → 4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-(3-aminophenyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol (913640-04-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogenchloride; tin(ll) chloride / water / 0.75 h / 90 °C

1.2: pH ~ 10

2.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 12 h / 25 °C

3.1: acetic acid / 24 h / 100 °C

3.2: 16 h / 20 °C

4.1: hydroxylamine hydrochloride; triethylamine / 1,4-dioxane / 12 h / 100 °C

5.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 70 °C

6.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 12 h / 70 °C

With 4-methyl-morpholine; hydrogenchloride; hydroxylamine hydrochloride; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; tin(ll) chloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; N,N-dimethyl-formamide;

upstream raw materials:

2-methyl-but-3-yn-2-ol

4-[2-(4-amino-1,2,5-oxadiazol-3-yl)-6-chloro-1-ethyl-1H-imidazo[4,5-c]pyridin-4-yl]-2-methyl-3-butyn-2-ol

3-Aminophenylboronic acid

2-bromo-N-ethyl-5-nitro-4-pyridinamine

Downstream raw materials:

1,1-dimethylethyl [2-({3-[2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-4-(3-hydroxy-3-methyl-1-butyn-1-yl)-1H-imidazo[4,5-c]pyridin-6-yl]phenyl}amino)-2-oxoethyl]carbamate