N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide

Base Information

• Chemical Name: N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide
• CAS No.: 1383853-93-7
• Molecular Formula: C₂₉H₂₆FN₃O₆S
• Molecular Weight: 563.606
• Mol file: 1383853-93-7.mol

Synonyms:N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide

Chemical Property of N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide

There total 16 articles about N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide 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: 35.0%

5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-6-[(4-methoxybenzyl)(methylsulfonyl)amino]-1-benzofuran-3-carboximidamide (1383851-52-2) + chloroacetyl chloride (79-04-9) → N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide (1383853-93-7)

Guidance literature:

5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-6-[(4-methoxybenzyl)(methylsulfonyl)amino]-1-benzofuran-3-carboximidamide; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

chloroacetyl chloride; With sodium hydride; In tetrahydrofuran; at 5 - 20 ℃; for 16h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; pH=7; Inert atmosphere;

Reference yield:

1-(4-fluorophenyl)ethanone (403-42-9) → N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide (1383853-93-7)

Guidance literature:

Multi-step reaction with 16 steps

1.1: potassium tert-butylate / toluene / 78 °C / Inert atmosphere

1.2: 78 °C / Inert atmosphere

1.3: 78 °C / Inert atmosphere

2.1: zinc(II) chloride / tetrahydrofuran; toluene / 6 h / Reflux; Inert atmosphere

3.1: 1-methyl-pyrrolidin-2-one; caesium carbonate / 4 h / 50 °C / Inert atmosphere

4.1: nitric acid / chloroform / 1 h / 0 - 20 °C

5.1: boron trichloride / dichloromethane / 1 h / 0 - 20 °C

5.2: 20 °C

6.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h

7.1: potassium fluoride dihydrate; sodium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel

8.1: iron; ammonium chloride / tetrahydrofuran; ethanol; water / 1.5 h / Inert atmosphere; Reflux

9.1: pyridine / dichloromethane / 3.33 h / 20 °C / Inert atmosphere

10.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 °C

11.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 10 - 20 °C / Inert atmosphere

11.2: 20 °C / Inert atmosphere

12.1: dipyridinium dichromate / dichloromethane / 18 h / 20 °C

13.1: hydroxylamine hydrochloride; sodium carbonate / ethanol; water / 2 h / Reflux

14.1: acetic anhydride / 16 h / 140 °C

15.1: hydroxylamine / ethanol; water / 0.5 h / 140 °C / sealed vial; microwave reactor

16.1: tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

16.2: 16 h / 5 - 20 °C / Inert atmosphere

16.3: 20 °C / pH 7 / Inert atmosphere

With pyridine; 1-methyl-pyrrolidin-2-one; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; potassium fluoride dihydrate; hydroxylamine hydrochloride; potassium tert-butylate; hydroxylamine; nitric acid; acetic anhydride; boron trichloride; iron; sodium carbonate; potassium carbonate; ammonium chloride; caesium carbonate; N-ethyl-N,N-diisopropylamine; sodium bromide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;

Reference yield:

ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4) → N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide (1383853-93-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: zinc(II) chloride / tetrahydrofuran; toluene / 6 h / Reflux; Inert atmosphere

2.1: 1-methyl-pyrrolidin-2-one; caesium carbonate / 4 h / 50 °C / Inert atmosphere

3.1: nitric acid / chloroform / 1 h / 0 - 20 °C

4.1: boron trichloride / dichloromethane / 1 h / 0 - 20 °C

4.2: 20 °C

5.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h

6.1: potassium fluoride dihydrate; sodium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 18 h / 125 °C / Inert atmosphere; sealed vessel

7.1: iron; ammonium chloride / tetrahydrofuran; ethanol; water / 1.5 h / Inert atmosphere; Reflux

8.1: pyridine / dichloromethane / 3.33 h / 20 °C / Inert atmosphere

9.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 °C

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 10 - 20 °C / Inert atmosphere

10.2: 20 °C / Inert atmosphere

11.1: dipyridinium dichromate / dichloromethane / 18 h / 20 °C

12.1: hydroxylamine hydrochloride; sodium carbonate / ethanol; water / 2 h / Reflux

13.1: acetic anhydride / 16 h / 140 °C

14.1: hydroxylamine / ethanol; water / 0.5 h / 140 °C / sealed vial; microwave reactor

15.1: tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

15.2: 16 h / 5 - 20 °C / Inert atmosphere

15.3: 20 °C / pH 7 / Inert atmosphere

With pyridine; 1-methyl-pyrrolidin-2-one; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; potassium fluoride dihydrate; hydroxylamine hydrochloride; hydroxylamine; nitric acid; acetic anhydride; boron trichloride; iron; sodium carbonate; potassium carbonate; ammonium chloride; caesium carbonate; N-ethyl-N,N-diisopropylamine; sodium bromide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

1-(4-fluorophenyl)ethanone

5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-6-[(4-methoxybenzyl)(methylsulfonyl)amino]-1-benzofuran-3-carboximidamide

chloroacetyl chloride

ethyl 3-(4'-fluorophenyl)-3-oxopropionate