ethyl 5-(7-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate

Base Information

• Chemical Name: ethyl 5-(7-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate
• CAS No.: 847671-80-1
• Molecular Formula: C₂₄H₂₄N₄O₇
• Molecular Weight: 480.477

Synonyms:ethyl 5-(7-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate

Chemical Property of ethyl 5-(7-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate

Chemical Property:

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Technology Process of ethyl 5-(7-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate

There total 4 articles about ethyl 5-(7-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate 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: 67.0%

4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoic acid (189365-92-2) + ethyl 5-(7-amino-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate (847671-79-8) → ethyl 5-(7-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate (847671-80-1)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at -10 - 20 ℃; pH=8;

DOI:10.1016/j.ejmech.2004.09.004

Reference yield:

7-nitro-4H-benzo[1,4]oxazin-3-one (81721-86-0) → ethyl 5-(7-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate (847671-80-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / K₂CO₃; benzyltriethylammonium chloride / acetonitrile / 48 h / 75 °C

2: 98 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

3: 67 percent / N-ethyl-N'-(dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole monohydrate; N-methylmorpholine / dimethylformamide / -10 - 20 °C / pH 8

With 4-methyl-morpholine; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.ejmech.2004.09.004

Reference yield:

5-Nitro-2-aminophenol (121-88-0) → ethyl 5-(7-{[4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoyl]amino}-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate (847671-80-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / KF / dimethylformamide / 20 - 60 °C

2: 79 percent / K₂CO₃; benzyltriethylammonium chloride / acetonitrile / 48 h / 75 °C

3: 98 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

4: 67 percent / N-ethyl-N'-(dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole monohydrate; N-methylmorpholine / dimethylformamide / -10 - 20 °C / pH 8

With 4-methyl-morpholine; potassium fluoride; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.ejmech.2004.09.004

upstream raw materials:

4-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)benzoic acid

ethyl 5-(7-amino-2H-1,4-benzoxazin-3(4H)-on-4-yl)pentanoate

7-nitro-4H-benzo[1,4]oxazin-3-one

5-Nitro-2-aminophenol

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