N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea

Base Information

Chemical Name:N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea
CAS No.:206000-80-8
Molecular Formula:C₃₁H₃₇N₅O₅
Molecular Weight:559.665
Hs Code.:

N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea

Synonyms:N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea

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Chemical Property of N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea

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Technology Process of N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea

There total 11 articles about N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea 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: 59.3%

: 108-24-7
acetic anhydride

: 205992-29-6
N-[(3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-5,9-dimethyl-1H-1,4-benzodiazepin-2-one-4-oxido-3-yl]-N'-(3-methylphenyl)urea

: 206000-80-8
N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea

Guidance literature:: at 50 ℃; for 5h;
DOI:10.1248/cpb.48.1

Reference yield:

: 53657-94-6
2-methyl-6-acetylaniline

: 206000-80-8
N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea

Guidance literature:: Multi-step reaction with 9 steps

1.1: N-methylmorpholine / tetrahydrofuran / 0 - 20 °C

2.1: 6.17 g / NH₃ / methanol / 20 °C

3.1: NaH / dimethylformamide / 4 h / 0 - 20 °C

3.2: 100 percent / dimethylformamide / 5.5 h / 20 °C

4.1: 84.2 percent / 1 N aq. NaOH / 1,2-dimethoxy-ethane / 20 °C

5.1: 79.9 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl; HOBT; Et₃N / dimethylformamide / 20 °C

6.1: 87 percent / ammonium formate / 10 percent Pd/C / ethanol / 1 h / 20 °C

7.1: 97.9 percent / tetrahydrofuran / 1 h / 20 °C

8.1: 48 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 9 h / 20 °C

9.1: 59.3 percent / 5 h / 50 °C

With 4-methyl-morpholine; sodium hydroxide; ammonia; ammonium formate; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: Cyclization / 3.1: deprotonation / 3.2: Alkylation / 4.1: Hydrolysis / 5.1: amidation / 6.1: Hydrogenolysis / 7.1: Addition / 8.1: Oxidation / 9.1: Acetoxylation;
DOI:10.1248/cpb.48.1

Reference yield:

: 95-53-4
o-toluidine

: 206000-80-8
N-[(3RS)-5-acetoxymethyl-1-(3-azabicyclo[3.2.2]nonan-3-yl)carbonylmethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one-3-yl]-N'-(3-methylphenyl)urea

Guidance literature:: Multi-step reaction with 10 steps

1.1: BCl₃ / toluene / 1 h / 20 °C

1.2: AlCl₃ / acetonitrile / 5 h / Heating

1.3: 39.8 percent / 2 N aq. HCl / acetonitrile / 2.5 h / Heating

2.1: N-methylmorpholine / tetrahydrofuran / 0 - 20 °C

3.1: 6.17 g / NH₃ / methanol / 20 °C

4.1: NaH / dimethylformamide / 4 h / 0 - 20 °C

4.2: 100 percent / dimethylformamide / 5.5 h / 20 °C

5.1: 84.2 percent / 1 N aq. NaOH / 1,2-dimethoxy-ethane / 20 °C

6.1: 79.9 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl; HOBT; Et₃N / dimethylformamide / 20 °C

7.1: 87 percent / ammonium formate / 10 percent Pd/C / ethanol / 1 h / 20 °C

8.1: 97.9 percent / tetrahydrofuran / 1 h / 20 °C

9.1: 48 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 9 h / 20 °C

10.1: 59.3 percent / 5 h / 50 °C

With 4-methyl-morpholine; sodium hydroxide; ammonia; ammonium formate; boron trichloride; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Addition / 1.2: Rearrangement / 1.3: Hydrolysis / 2.1: Acylation / 3.1: Cyclization / 4.1: deprotonation / 4.2: Alkylation / 5.1: Hydrolysis / 6.1: amidation / 7.1: Hydrogenolysis / 8.1: Addition / 9.1: Oxidation / 10.1: Acetoxylation;
DOI:10.1248/cpb.48.1