5-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Base Information

• Chemical Name: 5-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• CAS No.: 146981-08-0
• Molecular Formula: C₂₀H₂₅FN₄O₄
• Molecular Weight: 404.441
• Mol file: 146981-08-0.mol

Synonyms:

Chemical Property of 5-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 4.53E-19mmHg at 25°C
• Boiling Point: 673.7°Cat760mmHg
• Flash Point: 361.2°C
• Density: 1.431g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

There total 10 articles about 5-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-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:

3-methoxy-2,4,5-trifluorobenzoic acid (112811-65-1) → 5-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-<(3-aminomethyl)-3-methyl-1-pyrrolidinyl>-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (146981-08-0)

Guidance literature:

Multi-step reaction with 9 steps

1: oxalyl chloride, DMF / CH₂Cl₂ / 18 h / Ambient temperature

2: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h

3: acetic anhydride / 22 h / Heating

4: ethanol / 18 h / Ambient temperature

5: 81 percent / NaH / tetrahydrofuran / 18 h

6: 70 percent / KNO₃, conc. H₂SO₄ / 18 h / Ambient temperature

7: 36 percent / H₂ / Raney nickel / tetrahydrofuran / 7 h / 21 - 28 °C / 982.6 - 2585.7 Torr

8: 90 percent / 1.0N aq. NaOH / ethanol / 18 h / Ambient temperature

9: 1.) Et₃N, 2.) TFA / 1.) DMSO, CH₃CN, RT, 18 h, 2.) CH₂Cl₂, RT, 0.5 h

With [2,2]bipyridinyl; sodium hydroxide; n-butyllithium; oxalyl dichloride; sulfuric acid; hydrogen; acetic anhydride; sodium hydride; potassium nitrate; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; nickel; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jm00022a013

Reference yield:

2,4,5-trifluoro-3-methoxybenzoyl chloride (112811-66-2) → 5-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-<(3-aminomethyl)-3-methyl-1-pyrrolidinyl>-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (146981-08-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h

2: acetic anhydride / 22 h / Heating

3: ethanol / 18 h / Ambient temperature

4: 81 percent / NaH / tetrahydrofuran / 18 h

5: 70 percent / KNO₃, conc. H₂SO₄ / 18 h / Ambient temperature

6: 36 percent / H₂ / Raney nickel / tetrahydrofuran / 7 h / 21 - 28 °C / 982.6 - 2585.7 Torr

7: 90 percent / 1.0N aq. NaOH / ethanol / 18 h / Ambient temperature

8: 1.) Et₃N, 2.) TFA / 1.) DMSO, CH₃CN, RT, 18 h, 2.) CH₂Cl₂, RT, 0.5 h

With [2,2]bipyridinyl; sodium hydroxide; n-butyllithium; sulfuric acid; hydrogen; acetic anhydride; sodium hydride; potassium nitrate; triethylamine; trifluoroacetic acid; nickel; In tetrahydrofuran; ethanol;

DOI:10.1021/jm00022a013

Reference yield:

methyl 3-methoxy-2,4,5-trifluorobenzoate (136897-64-8) → 5-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-<(3-aminomethyl)-3-methyl-1-pyrrolidinyl>-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (146981-08-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 61 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature

2: oxalyl chloride, DMF / CH₂Cl₂ / 18 h / Ambient temperature

3: 1.) n-BuLi, 2,2'-bipyridyl / 1.) THF, hexane, from -20 deg C to -5 deg C, 2.) THF, hexane, -30 deg C, 2 h

4: acetic anhydride / 22 h / Heating

5: ethanol / 18 h / Ambient temperature

6: 81 percent / NaH / tetrahydrofuran / 18 h

7: 70 percent / KNO₃, conc. H₂SO₄ / 18 h / Ambient temperature

8: 36 percent / H₂ / Raney nickel / tetrahydrofuran / 7 h / 21 - 28 °C / 982.6 - 2585.7 Torr

9: 90 percent / 1.0N aq. NaOH / ethanol / 18 h / Ambient temperature

10: 1.) Et₃N, 2.) TFA / 1.) DMSO, CH₃CN, RT, 18 h, 2.) CH₂Cl₂, RT, 0.5 h

With [2,2]bipyridinyl; sodium hydroxide; n-butyllithium; oxalyl dichloride; sulfuric acid; hydrogen; acetic anhydride; sodium hydride; potassium nitrate; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jm00022a013

upstream raw materials:

3-<methyl>-3-methylpyrrolidine

5-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid

3-methoxy-2,4,5-trifluorobenzoic acid

2,4,5-trifluoro-3-methoxybenzoyl chloride

Refernces