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

Base Information

• Chemical Name: 5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-6-[(methylsulfonyl)(3-sulfamoylpropyl)amino]-1-benzofuran-3-carboximidamide
• CAS No.: 1383851-91-9
• Molecular Formula: C₂₂H₂₅FN₄O₆S₂
• Molecular Weight: 524.594

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 16 articles about 5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-6-[(methylsulfonyl)(3-sulfamoylpropyl)amino]-1-benzofuran-3-carboximidamide 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: 100.0%

3-{[3-cyano-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino}propane-1-sulfonamide (1383851-90-8) → 5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-6-[(methylsulfonyl)(3-sulfamoylpropyl)amino]-1-benzofuran-3-carboximidamide (1383851-91-9)

Guidance literature:

With hydroxylamine; In ethanol; water; at 140 ℃; for 0.5h; sealed tube; microwave reactor;

Reference yield:

1-(4-fluorophenyl)ethanone (403-42-9) → 5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-6-[(methylsulfonyl)(3-sulfamoylpropyl)amino]-1-benzofuran-3-carboximidamide (1383851-91-9)

Guidance literature:

Multi-step reaction with 17 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 / 0.5 h / 20 °C / Inert atmosphere

16.2: 67 h / 50 °C / Inert atmosphere

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

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; 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) → 5-cyclopropyl-2-(4-fluorophenyl)-N'-hydroxy-6-[(methylsulfonyl)(3-sulfamoylpropyl)amino]-1-benzofuran-3-carboximidamide (1383851-91-9)

Guidance literature:

Multi-step reaction with 16 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 / 0.5 h / 20 °C / Inert atmosphere

15.2: 67 h / 50 °C / Inert atmosphere

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

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; 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

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

ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate

ethyl 2-(4-fluorophenyl)-5-hydroxy-6-nitrobenzofuran-3-carboxylate

Downstream raw materials:

3-{[5-cyclopropyl-3-(4,5-dihydro-1,2,4-oxadiazol-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino}propane-1-sulfonamide

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