3-(4-fluorobenzyl)-N-(2-methoxyethyl)-N-methyl-6-oxo-7-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][ 1,7]naphthyridine-1-sulfonamide

Base Information

• Chemical Name: 3-(4-fluorobenzyl)-N-(2-methoxyethyl)-N-methyl-6-oxo-7-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][ 1,7]naphthyridine-1-sulfonamide
• CAS No.: 1293388-44-9
• Molecular Formula: C₂₆H₃₁FN₄O₆S
• Molecular Weight: 546.62

Synonyms:3-(4-fluorobenzyl)-N-(2-methoxyethyl)-N-methyl-6-oxo-7-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][ 1,7]naphthyridine-1-sulfonamide

Chemical Property of 3-(4-fluorobenzyl)-N-(2-methoxyethyl)-N-methyl-6-oxo-7-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][ 1,7]naphthyridine-1-sulfonamide

Chemical Property:

Purity/Quality:

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Technology Process of 3-(4-fluorobenzyl)-N-(2-methoxyethyl)-N-methyl-6-oxo-7-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][ 1,7]naphthyridine-1-sulfonamide

There total 15 articles about 3-(4-fluorobenzyl)-N-(2-methoxyethyl)-N-methyl-6-oxo-7-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][ 1,7]naphthyridine-1-sulfonamide 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: 37.0%

1-(4-fluorobenzyl)-4-(2-hydroxyethyl)-3-[ (2-methoxyethyl)(methyl)sulfamoyl]-N-(tetrahydro-2H-pyran-2-yloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxamide (1293388-40-5) → 3-(4-fluorobenzyl)-N-(2-methoxyethyl)-N-methyl-6-oxo-7-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][ 1,7]naphthyridine-1-sulfonamide (1293388-44-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃;

DOI:10.1021/jm200208d

Reference yield:

2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (936-12-9) → 3-(4-fluorobenzyl)-N-(2-methoxyethyl)-N-methyl-6-oxo-7-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][ 1,7]naphthyridine-1-sulfonamide (1293388-44-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / Inert atmosphere

1.2: 16.75 h / 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide / ethyl acetate / 1.75 h / 20 °C

2.2: 1.5 h / Reflux

3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h

3.2: 17 h / 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere

5.1: palladium 10% on activated carbon; hydrogen; triethylamine / methanol / 1 h / 2068.65 Torr / Inert atmosphere

6.1: triethylamine / dichloromethane / 0 °C

7.1: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 18 h / 60 °C / Inert atmosphere

8.1: lithium hydroxide / methanol; water / 5 h / 60 °C

9.1: acetic acid / 6 h / Reflux

10.1: 5 % alumina-supported palladium; hydrogen / tetrahydrofuran; methanol; water / 18 h / 1810.07 Torr / Inert atmosphere

11.1: chlorosulfonic acid; thionyl chloride / 20 °C

12.1: triethylamine / N,N-dimethyl-formamide / 20 °C

13.1: lithium hexamethyldisilazane / tetrahydrofuran

14.1: N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride / dichloromethane / 20 °C

With chlorosulfonic acid; bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; thionyl chloride; 5 % alumina-supported palladium; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; lithium chloride; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 7.1: Stille coupling;

DOI:10.1021/jm200208d

Reference yield:

7-(4-fluorobenzyl)pyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(7H)-one (868660-36-0) → 3-(4-fluorobenzyl)-N-(2-methoxyethyl)-N-methyl-6-oxo-7-(tetrahydro-2H-pyran-2-yloxy)-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][ 1,7]naphthyridine-1-sulfonamide (1293388-44-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 5 % alumina-supported palladium; hydrogen / tetrahydrofuran; methanol; water / 18 h / 1810.07 Torr / Inert atmosphere

2: chlorosulfonic acid; thionyl chloride / 20 °C

3: triethylamine / N,N-dimethyl-formamide / 20 °C

4: lithium hexamethyldisilazane / tetrahydrofuran

5: N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride / dichloromethane / 20 °C

With chlorosulfonic acid; thionyl chloride; 5 % alumina-supported palladium; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm200208d

upstream raw materials:

2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

7-(4-fluorobenzyl)pyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(7H)-one

7-(4-fluorobenzyl)-1,7-dihydropyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(2H)-one

7-(4-fluorobenzyl)-4-oxo-1,2,4,7-tetrahydropyrano[3,4-b]pyrrolo[3,2-d]pyridine-9-sulfonyl chloride

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