(2'R,4'S)-7-<4'-amino-2'-(fluoromethyl)pyrrolidinyl>-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'-(fluoromethyl)pyrrolidinyl>-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride
CAS No.:114676-90-3
Molecular Formula:C₂₀H₁₆F₄N₄O₃*ClH
Molecular Weight:472.827
Hs Code.:

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

There total 13 articles about (2'R,4'S)-7-<4'-amino-2'-(fluoromethyl)pyrrolidinyl>-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:

: 100491-29-0
ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

: 114676-90-3
(2'R,4'S)-7-<4'-amino-2'-(fluoromethyl)pyrrolidinyl>-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / pyridine / 48 h / 40 °C

2: 1.) aq. NaOH, 2.) aq. HCl / 1.) THF, 60 deg C, 4.5 h, 2.) 105 deg C, 17 h

With hydrogenchloride; sodium hydroxide; triethylamine; In pyridine;
DOI:10.1021/jm00403a020

Reference yield:

: 114676-69-6
(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

: 114676-90-3
(2'R,4'S)-7-<4'-amino-2'-(fluoromethyl)pyrrolidinyl>-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) pyridinium p-toluenesulfonate, 2.) lithium borohydride / 1.) dichloromethane, room temperature 3 h, 2.) THF

2: 7.5 g / triethylamine / CH₂Cl₂ / 1 h / 0 °C

3: 62 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Heating

4: 60 percent / acetic acid / H₂O / 1.5 h / Heating

5: 96 percent / triethylamine / CH₂Cl₂ / 14 h

6: 80 percent / tetra-n-butylammonium fluoride / acetonitrile / 3 h / 65 °C

7: 54 percent / 5 h

8: trifluoroacetic acid / 0.25 h

9: triethylamine / pyridine / 48 h / 40 °C

10: 1.) aq. NaOH, 2.) aq. HCl / 1.) THF, 60 deg C, 4.5 h, 2.) 105 deg C, 17 h

With hydrogenchloride; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane; water; acetonitrile;
DOI:10.1021/jm00403a020

Reference yield:

: 114676-59-4
(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride

: 114676-90-3
(2'R,4'S)-7-<4'-amino-2'-(fluoromethyl)pyrrolidinyl>-1-(2,4-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid hydrochloride

Guidance literature:: Multi-step reaction with 11 steps

1: 90 percent / triethylamine / CH₂Cl₂ / 12 h

2: 1.) pyridinium p-toluenesulfonate, 2.) lithium borohydride / 1.) dichloromethane, room temperature 3 h, 2.) THF

3: 7.5 g / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4: 62 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Heating

5: 60 percent / acetic acid / H₂O / 1.5 h / Heating

6: 96 percent / triethylamine / CH₂Cl₂ / 14 h

7: 80 percent / tetra-n-butylammonium fluoride / acetonitrile / 3 h / 65 °C

8: 54 percent / 5 h

9: trifluoroacetic acid / 0.25 h

10: triethylamine / pyridine / 48 h / 40 °C

11: 1.) aq. NaOH, 2.) aq. HCl / 1.) THF, 60 deg C, 4.5 h, 2.) 105 deg C, 17 h

With hydrogenchloride; sodium hydroxide; lithium borohydride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane; water; acetonitrile;
DOI:10.1021/jm00403a020