N-[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)methanesulfonamide

Base Information

• Chemical Name: N-[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)methanesulfonamide
• CAS No.: 1383851-92-0
• Molecular Formula: C₂₄H₂₆FN₃O₅S
• Molecular Weight: 487.552
• Mol file: 1383851-92-0.mol

Synonyms:N-[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)methanesulfonamide

Chemical Property of N-[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)methanesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)methanesulfonamide

There total 19 articles about N-[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)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: 34.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-6-[(4-hydroxybutyl)(methylsulfonyl)amino]-1-benzofuran-3-carboximidamide (1383851-80-6) → N-[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)methanesulfonamide (1383851-92-0)

Guidance literature:

In ethanol; water; at 130 ℃; for 1.5h; sealed tube; microwave tube;

Reference yield:

1-(4-fluorophenyl)ethanone (403-42-9) → N-[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)methanesulfonamide (1383851-92-0)

Guidance literature:

Multi-step reaction with 19 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: trifluoroacetic acid / dichloromethane / 3 h / Cooling with ice

16.1: potassium carbonate / dimethyl sulfoxide / 16.5 h / 50 °C / microwave tube; sealed tube

17.1: hydroxylamine / ethanol; water / 0.5 h / 140 °C / sealed tube; microwave tube

18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

19.1: ethanol; water / 1.5 h / 130 °C / sealed tube; microwave tube

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

Reference yield:

ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4) → N-[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)methanesulfonamide (1383851-92-0)

Guidance literature:

Multi-step reaction with 18 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: trifluoroacetic acid / dichloromethane / 3 h / Cooling with ice

15.1: potassium carbonate / dimethyl sulfoxide / 16.5 h / 50 °C / microwave tube; sealed tube

16.1: hydroxylamine / ethanol; water / 0.5 h / 140 °C / sealed tube; microwave tube

17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

18.1: ethanol; water / 1.5 h / 130 °C / sealed tube; microwave tube

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

upstream raw materials:

1-(4-fluorophenyl)ethanone

formaldehyd

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

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