3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)amino]methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: 3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)amino]methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester
• CAS No.: 1418025-06-5
• Molecular Formula: C₂₈H₂₄F₃N₅O₅
• Molecular Weight: 567.524

Synonyms:3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)amino]methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester

Chemical Property of 3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)amino]methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)amino]methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester

There total 10 articles about 3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)amino]methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester 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:

6-morpholin-4-ylpyridine-3-carboxylic acid (120800-52-4) + 3-aminomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester hydrochloride (1418026-06-8) → 3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)amino]methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (1418025-06-5)

Guidance literature:

6-morpholin-4-ylpyridine-3-carboxylic acid; With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 0.75h; under 760.051 Torr; Inert atmosphere;

3-aminomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester hydrochloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; under 760.051 Torr; Inert atmosphere;

Reference yield:

aniline (62-53-3) → 3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)amino]methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (1418025-06-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C / 760.05 Torr / Inert atmosphere

1.2: -78 - 20 °C / 760.05 Torr / Inert atmosphere

1.3: 760.05 Torr / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 25 °C / 760.05 Torr / Inert atmosphere

3.1: tetrahydrofuran / 4.5 h / 0 - 20 °C / 760.05 Torr / Inert atmosphere

4.1: toluene / 18 h / 760.05 Torr / Inert atmosphere; Reflux

5.1: potassium carbonate / methanol / 2 h / 760.05 Torr / Inert atmosphere; Reflux

6.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / 760.05 Torr / Inert atmosphere; Reflux

7.1: sodium azide / N,N-dimethyl-formamide / 16 h / 22 °C / 760.05 Torr / Inert atmosphere

8.1: platinum(IV) oxide; hydrogen; hydrogenchloride / 1,4-dioxane; ethyl acetate / 11 h / 25 °C / 760.05 Torr / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.75 h / 20 °C / 760.05 Torr / Inert atmosphere

9.2: 0 - 20 °C / 760.05 Torr / Inert atmosphere

With hydrogenchloride; platinum(IV) oxide; N-Bromosuccinimide; sodium azide; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; lithium hexamethyldisilazane; dibenzoyl peroxide; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

Reference yield:

2-chloro-6-(trifluoromethyl)pyridine-3-carboxylic acid (280566-45-2) → 3-{[(6-morpholin-4-yl-pyridine-3-carbonyl)amino]methyl}-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (1418025-06-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C / 760.05 Torr / Inert atmosphere

1.2: -78 - 20 °C / 760.05 Torr / Inert atmosphere

1.3: 760.05 Torr / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 4 h / 25 °C / 760.05 Torr / Inert atmosphere

3.1: tetrahydrofuran / 4.5 h / 0 - 20 °C / 760.05 Torr / Inert atmosphere

4.1: toluene / 18 h / 760.05 Torr / Inert atmosphere; Reflux

5.1: potassium carbonate / methanol / 2 h / 760.05 Torr / Inert atmosphere; Reflux

6.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / 760.05 Torr / Inert atmosphere; Reflux

7.1: sodium azide / N,N-dimethyl-formamide / 16 h / 22 °C / 760.05 Torr / Inert atmosphere

8.1: platinum(IV) oxide; hydrogen; hydrogenchloride / 1,4-dioxane; ethyl acetate / 11 h / 25 °C / 760.05 Torr / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.75 h / 20 °C / 760.05 Torr / Inert atmosphere

9.2: 0 - 20 °C / 760.05 Torr / Inert atmosphere

With hydrogenchloride; platinum(IV) oxide; N-Bromosuccinimide; sodium azide; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; lithium hexamethyldisilazane; dibenzoyl peroxide; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

upstream raw materials:

6-morpholin-4-ylpyridine-3-carboxylic acid

3-aminomethyl-4-oxo-1-phenyl-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester hydrochloride

aniline

2-chloro-6-(trifluoromethyl)pyridine-3-carboxylic acid

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