1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Base Information

• Chemical Name: 1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine
• CAS No.: 163617-94-5
• Molecular Formula: C₃₂H₃₉N₅O₃
• Molecular Weight: 541.693
• Mol file: 163617-94-5.mol

Synonyms:1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Chemical Property of 1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

There total 6 articles about 1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine 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: 62.0%

N-(1-adamantyl)methyl-N'-[2-(morpholin-4-yl)ethyl]-1,2-phenylenediamine (163617-93-4) + 2-(phenylhydrazono)-propanedioyl dichloride (19288-90-5) → 1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (163617-94-5)

Guidance literature:

In ethyl acetate; for 2h; Reflux;

DOI:10.1016/j.bmc.2011.05.057

Reference yield:

2-nitro-aniline (88-74-4) → 1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (163617-94-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / acetone / 25 h / 23 - 70 °C / Inert atmosphere

2.1: dimethylsulfide borane complex / toluene / 1.25 h / 10 - 110 °C / Inert atmosphere

2.2: 0.67 h / 23 °C / Inert atmosphere

3.1: sodium dithionite; water; potassium carbonate / ethanol / 0.5 h / 23 °C

3.2: pH 3

3.3: pH 10

4.1: potassium carbonate; sodium iodide / 5,5-dimethyl-1,3-cyclohexadiene / 4 h / 160 °C / Inert atmosphere

5.1: ethyl acetate / 2 h / Reflux

With sodium dithionite; dimethylsulfide borane complex; water; potassium carbonate; triethylamine; sodium iodide; In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; ethyl acetate; acetone; toluene;

DOI:10.1016/j.bmc.2011.05.057

Reference yield:

1-Adamantanecarbonyl chloride (2094-72-6) → 1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-3-phenylhydrazono-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (163617-94-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / acetone / 25 h / 23 - 70 °C / Inert atmosphere

2.1: dimethylsulfide borane complex / toluene / 1.25 h / 10 - 110 °C / Inert atmosphere

2.2: 0.67 h / 23 °C / Inert atmosphere

3.1: sodium dithionite; water; potassium carbonate / ethanol / 0.5 h / 23 °C

3.2: pH 3

3.3: pH 10

4.1: potassium carbonate; sodium iodide / 5,5-dimethyl-1,3-cyclohexadiene / 4 h / 160 °C / Inert atmosphere

5.1: ethyl acetate / 2 h / Reflux

With sodium dithionite; dimethylsulfide borane complex; water; potassium carbonate; triethylamine; sodium iodide; In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; ethyl acetate; acetone; toluene;

DOI:10.1016/j.bmc.2011.05.057

upstream raw materials:

N-(1-adamantyl)methyl-N'-[2-(morpholin-4-yl)ethyl]-1,2-phenylenediamine

2-(phenylhydrazono)-propanedioyl dichloride

1-Adamantanecarbonyl chloride

2-nitro-aniline

Downstream raw materials:

2-tert-butoxycarbonylamino-N-([1-(1-adamantylmethyl)-5-[2-(morpholin-4-yl)ethyl]-2,4-dioxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl])-3-phenylpropionamide

N-{1-(1-adamantyl)methyl-2,4-dioxo-5-[2-(morpholin-4-yl)ethyl]-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl}-N'-phenylurea