N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]methanesulfonamide

Base Information

• Chemical Name: N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]methanesulfonamide
• CAS No.: 1445993-15-6
• Molecular Formula: C₂₀H₂₃N₃O₅S
• Molecular Weight: 417.486

Synonyms:N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]methanesulfonamide

Chemical Property of N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]methanesulfonamide

Chemical Property:

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Technology Process of N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]methanesulfonamide

There total 8 articles about N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]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: 47.0%

4-(5-amino-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (1445994-30-8) + methanesulfonyl chloride (124-63-0) → N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]methanesulfonamide (1445993-15-6)

Guidance literature:

4-(5-amino-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one; methanesulfonyl chloride; With triethylamine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

With sodium hydroxide; In 1,4-dioxane; water; at 60 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b00746

Reference yield:

4-(2-fluoro-5-nitrophenyl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]-pyridin-7(6H)-one (1445993-88-3) → N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]methanesulfonamide (1445993-15-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / mineral oil; tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 2 h / 50 °C / Inert atmosphere

2.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 16 h

3.1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

3.2: 1 h / 60 °C / Inert atmosphere

With palladium 10% on activated carbon; hydrogen; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; mineral oil;

DOI:10.1021/acs.jmedchem.7b00746

Reference yield:

(E)-2-(5-bromo-2-methoxy-3-nitropyridin-4-yl)-N,N-dimethylethylene-1-amine → N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]methanesulfonamide (1445993-15-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Ra-Ni 2800 / water; ethyl acetate / 0.5 h / 20 °C / 1551.49 Torr / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

3.1: hydrogenchloride / 1,4-dioxane / 16 h / 40 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / Inert atmosphere

4.2: 3 h / 20 °C / Inert atmosphere

5.1: sodium carbonate / 1,2-dimethoxyethane; water / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere; Sealed tube

6.1: sodium hydride / mineral oil; tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

6.2: 2 h / 50 °C / Inert atmosphere

7.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 16 h

8.1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

8.2: 1 h / 60 °C / Inert atmosphere

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; sodium hydride; sodium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil; 5.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.7b00746

upstream raw materials:

4-(2-fluoro-5-nitrophenyl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]-pyridin-7(6H)-one

5-bromo-2-methoxy-4-methyl-3-nitropyridine

4-(5-amino-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

methanesulfonyl chloride

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