1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid

Base Information

• Chemical Name: 1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid
• CAS No.: 908340-17-0
• Molecular Formula: C₂₁H₂₂FN₃O₆
• Molecular Weight: 431.421

Synonyms:1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid

Chemical Property of 1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid

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Technology Process of 1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid

There total 2 articles about 1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid 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: 92.0%

1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester (908340-16-9) → 1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid (908340-17-0)

Guidance literature:

With lithium hydroxide; In ethanol; for 24h;

DOI:10.1021/jm060010w

Reference yield:

7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester (110286-57-2) → 1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid (908340-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Et₃N / acetonitrile / 18 h / 25 °C

2: 92 percent / aq. LiOH / ethanol / 24 h

With lithium hydroxide; triethylamine; In ethanol; acetonitrile;

DOI:10.1021/jm060010w

Reference yield: 30.0%

1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid (908340-17-0) → 5-(2,4-dimethoxybenzyl)-4-methyl-8-oxo-3,4,5,8-tetrahydro-2H-1-oxa-4,5,10-triazaanthracene-7-carboxylic acid (866926-18-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 90 - 115 ℃;

DOI:10.1021/jm060010w

upstream raw materials:

1-(2,4-dimethoxybenzyl)-6-fluoro-7-[(2-hydroxyethyl)methylamino]-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

Downstream raw materials:

5-(2,4-dimethoxybenzyl)-4-methyl-8-oxo-3,4,5,8-tetrahydro-2H-1-oxa-4,5,10-triazaanthracene-7-carboxylic acid

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