8-[(3S)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride (1:1)

Base Information

• Chemical Name: 8-[(3S)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride (1:1)
• CAS No.: 162763-53-3
• Molecular Formula: 20C₁₈H₂₀FN₃O₃*23ClH
• Molecular Weight: 7746.07
• Mol file: 162763-53-3.mol

Synonyms:4H-Quinolizine-3-carboxylicacid, 8-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-,monohydrochloride, (S)-; 4H-Quinolizine-3-carboxylic acid,8-[(3S)-3-amino-1-pyrrolidinyl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-,monohydrochloride (9CI); A 86719.1; ABT 719

Chemical Property of 8-[(3S)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride (1:1)

Chemical Property:

• Vapor Pressure: 2.03E-11mmHg at 25°C
• Boiling Point: 501.5°C at 760 mmHg
• Flash Point: 257.1°C

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-[(3S)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride (1:1)

There total 51 articles about 8-[(3S)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride (1:1) 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:

3-chloro-2,4,5,6-tetrafluoropyridine (1735-84-8) → (S)-8-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride (162763-53-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 53 percent / tetrahydrofuran / 16 h / Ambient temperature

2: 83 percent / H₂, Et₃N / 10percent Pd(OH)2/C / ethyl acetate / 18 h / 3040 Torr / Ambient temperature

3: 1.) LDA / 1.) THF, -78 deg C, 25 min, 2.) THF, a) -78 deg C, 30 min, b) RT, 30 min

4: 1.) N₂H₄*H₂O, 2.) O₂, 20percent aq. NaOH / 1.) n-PrOH, reflux, 3 h, 2.) MeOH, 3 d

5: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h

6: CF₃COOH / 1 h / Ambient temperature

7: POCl₃, DMF / CH₂Cl₂

8: 88 percent / aq. HCl / 3 h / 80 - 85 °C

9: LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

10: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to -10 deg C, 15 min

11: piperidine, AcOH / ethanol / 5 h / Heating

12: biphenyl; diphenyl ether / 0.5 h / 235 - 240 °C

13: NaHCO₃ / acetonitrile / 4 h / Heating

14: aq. LiOH / tetrahydrofuran / 10 h / 60 °C

15: HCl, AcOH / CH₂Cl₂ / 0.67 h / Ambient temperature

With piperidine; hydrogenchloride; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; oxygen; sodium hydrogencarbonate; hydrazine hydrate; acetic acid; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; lithium diisopropyl amide; trichlorophosphate; palladium dihydroxide; In tetrahydrofuran; diphenylether; biphenyl; ethanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/jm960207w

Reference yield:

3-chloro-2,4,5,6-tetrafluoropyridine (1735-84-8) → A-86504.1 (162763-53-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 53 percent / tetrahydrofuran / 16 h / Ambient temperature

2: 83 percent / H₂, Et₃N / 10percent Pd(OH)2/C / ethyl acetate / 18 h / 3040 Torr / Ambient temperature

3: 1.) LDA / 1.) THF, -78 deg C, 25 min, 2.) THF, a) -78 deg C, 30 min, b) RT, 30 min

4: 1.) N₂H₄*H₂O, 2.) O₂, 20percent aq. NaOH / 1.) n-PrOH, reflux, 3 h, 2.) MeOH, 3 d

5: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h

6: CF₃COOH / 1 h / Ambient temperature

7: POCl₃, DMF / CH₂Cl₂

8: 88 percent / aq. HCl / 3 h / 80 - 85 °C

9: LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

10: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to -10 deg C, 15 min

11: piperidine, AcOH / ethanol / 5 h / Heating

12: biphenyl; diphenyl ether / 0.5 h / 235 - 240 °C

13: NaHCO₃ / acetonitrile / 4 h / Heating

14: aq. LiOH / tetrahydrofuran / 10 h / 60 °C

15: HCl, AcOH / CH₂Cl₂ / 0.67 h / Ambient temperature

With piperidine; hydrogenchloride; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; oxygen; sodium hydrogencarbonate; hydrazine hydrate; acetic acid; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; lithium diisopropyl amide; trichlorophosphate; palladium dihydroxide; In tetrahydrofuran; diphenylether; biphenyl; ethanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/jm960207w

Reference yield:

3-chloro-2,4,5,6-tetrafluoropyridine (1735-84-8) → A-87092.1 (162763-53-3)

Guidance literature:

Multi-step reaction with 15 steps

1: 53 percent / tetrahydrofuran / 16 h / Ambient temperature

2: 83 percent / H₂, Et₃N / 10percent Pd(OH)2/C / ethyl acetate / 18 h / 3040 Torr / Ambient temperature

3: 1.) LDA / 1.) THF, -78 deg C, 25 min, 2.) THF, a) -78 deg C, 30 min, b) RT, 30 min

4: 1.) N₂H₄*H₂O, 2.) O₂, 20percent aq. NaOH / 1.) n-PrOH, reflux, 3 h, 2.) MeOH, 3 d

5: 1.) LDA / 1.) THF, -78 deg C, 15 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h

6: CF₃COOH / 1 h / Ambient temperature

7: POCl₃, DMF / CH₂Cl₂

8: 88 percent / aq. HCl / 3 h / 80 - 85 °C

9: LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

10: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, from -78 deg C to -10 deg C, 15 min

11: piperidine, AcOH / ethanol / 5 h / Heating

12: biphenyl; diphenyl ether / 0.5 h / 235 - 240 °C

13: NaHCO₃ / acetonitrile / 4 h / Heating

14: aq. LiOH / tetrahydrofuran / 10 h / 60 °C

15: HCl, AcOH / CH₂Cl₂ / 0.67 h / Ambient temperature

With piperidine; hydrogenchloride; lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; oxygen; sodium hydrogencarbonate; hydrazine hydrate; acetic acid; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; lithium diisopropyl amide; trichlorophosphate; palladium dihydroxide; In tetrahydrofuran; diphenylether; biphenyl; ethanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/jm960207w

upstream raw materials:

8-((S)-3-tert-Butoxycarbonylamino-pyrrolidin-1-yl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid

2-cyclopropylacetonitrile

3-chloro-2,4,5,6-tetrafluoropyridine

4-t-butoxy-3-methyl-2,5-difluoropyridine

Refernces

• 1、 Li, Qun,Chu, Daniel T. W.,Claiborne, Akiyo,Cooper, Curt S.,Lee, Cheuk M.,Raye, Kathleen,Berst, Kristine B.,Donner, Pamela,Wang, Weibo,Hasvold, Lisa,Fung, Anthony,Ma, Zhenkun,Tufano, Michael,Flamm, Robert,Shen, Linus L.,Baranowski, John,Nilius, Angela,Alder, Jeff,Meulbroek, Jonathan,Marsh, Kennan,Crowell, DeAnne,Hui, Yuhua,Seif, Louis,Melcher, Laura M.,Henry, Rodger,Spanton, Steven,Faghih, Ramin,Klein, Larry L.,Tanaka, S. Ken,Plattner, Jacob J.. "Synthesis and structure-activity relationships of 2-pyridones: A novel series of potent DNA gyrase inhibitors as antibacterial agents". . p. 3070 - 3088. Retrieved 2007/10/03.