(2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

Base Information

Chemical Name:(2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride
CAS No.:114676-85-6
Molecular Formula:C₂₀H₁₇F₃N₄O₃*ClH
Molecular Weight:454.836
Hs Code.:

Synonyms:(2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

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Chemical Property of (2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

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Technology Process of (2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

There total 10 articles about (2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride 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:

: 1499-56-5,775275-31-5,790644-51-8,754962-86-2
(R)-4-hydroxy-L-proline ethyl ester

: 114676-85-6
(2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) triethylamine, 2.) imidazole / 1.) dichloromethane, 12 h, 2.) DMF, room temperature 1.5 h

2: lithium borohydride / tetrahydrofuran / 16 h

3: triethylamine / CH₂Cl₂ / 15 h

4: 1.) lithium triethylborohydride, 2.) tetra-n-butylammonium fluoride / 1.) THF, room temperature, 2.) 2.5 h

5: 1.) methanesulfonyl chloride, triethylamine, 2.) tetra-n-butylammonium azide / 1.) dichloromethane, 14 h, 2.) acetonitrile, 65 deg C, 3 h

6: 1.) hydrogen, 2.) triethylamine / 1.) 10percent palladium on carbon / 1.) methanol, 4 atm, 1 h, 2.) pyridine, room temperature, 19 h

7: hydrogen / palladium on carbon

8: triethylamine / pyridine / 336 h / 65 °C

9: 1.) aq. NaOH, 2.) aq. hydrochloric acid / 1.) THF, 65 deg C, 4 h, 2.) 110 deg C, 15 h

With 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; hydrogen; tetrabutylammoniun azide; lithium triethylborohydride; methanesulfonyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jm00403a020

Reference yield:

: 114676-91-4
1-tert-butyl 2-methyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate

: 114676-85-6
(2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

Guidance literature:: Multi-step reaction with 8 steps

1: lithium borohydride / tetrahydrofuran / 16 h

2: triethylamine / CH₂Cl₂ / 15 h

3: 1.) lithium triethylborohydride, 2.) tetra-n-butylammonium fluoride / 1.) THF, room temperature, 2.) 2.5 h

4: 1.) methanesulfonyl chloride, triethylamine, 2.) tetra-n-butylammonium azide / 1.) dichloromethane, 14 h, 2.) acetonitrile, 65 deg C, 3 h

5: 1.) hydrogen, 2.) triethylamine / 1.) 10percent palladium on carbon / 1.) methanol, 4 atm, 1 h, 2.) pyridine, room temperature, 19 h

6: hydrogen / palladium on carbon

7: triethylamine / pyridine / 336 h / 65 °C

8: 1.) aq. NaOH, 2.) aq. hydrochloric acid / 1.) THF, 65 deg C, 4 h, 2.) 110 deg C, 15 h

With hydrogenchloride; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; hydrogen; tetrabutylammoniun azide; lithium triethylborohydride; methanesulfonyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jm00403a020

Reference yield:

: 114676-67-4
(2S,4R)-1-Boc-4-[(t-butyldimethylsilyl)oxy]-2-(hydroxymethyl)pyrrolidine

: 114676-85-6
(2'R,4'S)-7-(4'-amino-2'-methylpyrrolidinyl)-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

Guidance literature:: Multi-step reaction with 7 steps

1: triethylamine / CH₂Cl₂ / 15 h

2: 1.) lithium triethylborohydride, 2.) tetra-n-butylammonium fluoride / 1.) THF, room temperature, 2.) 2.5 h

3: 1.) methanesulfonyl chloride, triethylamine, 2.) tetra-n-butylammonium azide / 1.) dichloromethane, 14 h, 2.) acetonitrile, 65 deg C, 3 h

4: 1.) hydrogen, 2.) triethylamine / 1.) 10percent palladium on carbon / 1.) methanol, 4 atm, 1 h, 2.) pyridine, room temperature, 19 h

5: hydrogen / palladium on carbon

6: triethylamine / pyridine / 336 h / 65 °C

7: 1.) aq. NaOH, 2.) aq. hydrochloric acid / 1.) THF, 65 deg C, 4 h, 2.) 110 deg C, 15 h

With hydrogenchloride; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; tetrabutylammoniun azide; lithium triethylborohydride; methanesulfonyl chloride; triethylamine; palladium on activated charcoal; In pyridine; dichloromethane;
DOI:10.1021/jm00403a020