5-Amino-7-[3(R)-(1-aminocyclopropyl)-4(S)-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Base Information

Chemical Name:5-Amino-7-[3(R)-(1-aminocyclopropyl)-4(S)-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
CAS No.:190954-07-5
Molecular Formula:C₂₁H₂₃F₃N₄O₃
Molecular Weight:436.434
Hs Code.:

5-Amino-7-[3(R)-(1-aminocyclopropyl)-4(S)-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

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Chemical Property of 5-Amino-7-[3(R)-(1-aminocyclopropyl)-4(S)-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

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Technology Process of 5-Amino-7-[3(R)-(1-aminocyclopropyl)-4(S)-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

There total 39 articles about 5-Amino-7-[3(R)-(1-aminocyclopropyl)-4(S)-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methyl-4-oxo-1,4-dihydroquinoline-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:

: 190954-43-9
ethyl 1-{(3S,4S)-4-fluoro-5-oxo-1-[(S)-1-phenylethyl]pyrrolidin-3-yl}cyclopropanecarboxylate

: 190954-07-5
5-amino-7-[(3S,4R)-4-(1-aminocycloprop-1-yl)-3-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocycloprop-1-yl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaOH; water / ethanol / 6 h / 40 °C

1.2: DPPA; Et₃N / toluene / 2 h / Heating

1.3: 73 percent / toluene / 21 h / Heating

2.1: BH₃*THF / tetrahydrofuran / 17 h / 20 °C

2.2: 99 percent / Et₃N / aq. ethanol / 2.5 h / Heating

3.1: 100 percent / H₂ / Pd/C / ethanol / 3 h / 40 °C

4.1: 520 mg / N-methylpiperidine; DMSO / 168 h / 75 °C

5.1: 243 mg / HCl; water / 0.33 h / 20 °C

With N-methylcyclohexylamine; hydrogenchloride; sodium hydroxide; borane-THF; water; hydrogen; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; ethanol;
DOI:10.3987/COM-03-9972

Reference yield:

: 181941-62-8
ethyl (E)-3-(1-ethoxycarbonylcyclopropan-1-yl)-2-butenoate

: 190954-07-5
5-amino-7-[(3R,4R)-4-(1-aminocyclopropan-1-yl)-3-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-1,4-dihydro-8-methyl-4-oxoquinolin-3-carboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: NBS; AIBN / CCl₄ / 5 h / Heating

2.1: 13.1 g / NaHCO₃ / ethanol / 4 h / Heating

3.1: 74 percent / H₂ / PtO₂ / methanol / 18 h / 20 °C

4.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: 71 percent / N-fluorobenzenesulfonimide / hexane; tetrahydrofuran / -78 - 20 °C

5.1: 89 percent / Lawesson's reagent / benzene / 3 h / Heating

6.1: 95 percent / Raney Ni W-6 / ethanol / 1 h / 20 °C

7.1: 89 percent / CH₂Cl₂ / 15 h / 40 °C

8.1: 98 percent / aq. NaOH / ethanol / 40 °C

9.1: 65 percent / Et₃N; diphenylphosphoryl azide / Heating

10.1: H₂; H₂O / 5percent Pd/C / methanol / 7 h / 20 °C / 3310.09 Torr

11.1: Et₃N / dimethylsulfoxide / 96 h / 120 °C

12.1: aq. HCl / 0.25 h / 20 °C

With Lawessons reagent; hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); Raney Ni W-6; diphenylphosphoranyl azide; water; hydrogen; sodium hydrogencarbonate; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; dimethyl sulfoxide; benzene; 9.1: Curtius rearrangement;
DOI:10.1021/jm020328y

Reference yield:

: 181941-62-8
ethyl (E)-3-(1-ethoxycarbonylcyclopropan-1-yl)-2-butenoate

: 190954-07-5
5-amino-7-[(3S,4R)-4-(1-aminocycloprop-1-yl)-3-fluoropyrrolidin-1-yl]-6-fluoro-1-[(1R,2S)-2-fluorocycloprop-1-yl]-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid

Guidance literature:: Multi-step reaction with 13 steps

1.1: NBS; AIBN / CCl₄ / 5 h / Heating

2.1: 13.1 g / NaHCO₃ / ethanol / 4 h / Heating

3.1: 74 percent / H₂ / PtO₂ / methanol / 18 h / 20 °C

4.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: 71 percent / N-fluorobenzenesulfonimide / hexane; tetrahydrofuran / -78 - 20 °C

5.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C

5.2: 74 percent / 2,6-di-t-butylphenol / tetrahydrofuran

6.1: 90 percent / Lawesson's reagent / benzene / Heating

7.1: 86 percent / Raney Ni W-6 / ethanol / 20 °C

8.1: 89 percent / CH₂Cl₂ / 40 °C

9.1: 92 percent / aq. NaOH / ethanol / 40 °C

10.1: 81 percent / Et₃N; diphenylphosphoryl azide / Heating

11.1: H₂; H₂O / 5percent Pd/C / methanol / Heating

12.1: Et₃N / dimethylsulfoxide / 150 °C

13.1: aq. HCl / 20 °C

With Lawessons reagent; hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); Raney Ni W-6; diphenylphosphoranyl azide; water; hydrogen; sodium hydrogencarbonate; triethylamine; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; dimethyl sulfoxide; benzene; 10.1: Curtius rearrangement;
DOI:10.1021/jm020328y