7-[(7s)-7-Amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1s,2r)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Base Information

• Chemical Name: 7-[(7s)-7-Amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1s,2r)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• CAS No.: 127254-11-9
• Molecular Formula: C₁₉H₁₈ClF₂N₃O₃
• Molecular Weight: 409.82
• DSSTox Substance ID: DTXSID801101677
• Nikkaji Number: J621.677C
• ChEMBL ID: CHEMBL607160
• Mol file: 127254-11-9.mol

Synonyms:127254-11-9;sitafloxacin isomer I(SSR);7-[(7s)-7-amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1s,2r)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid;DU 6856;7-((S)-7-amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-6-fluoro-1-((1S,2R)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;7-[(7S)-7-AMINO-5-AZASPIRO[2.4]HEPTAN-5-YL]-8-CHLORO-6-FLUORO-1-[(1S,2R)-2-FLUOROCYCLOPROPYL]-4-OXOQUINOLINE-3-CARBOXYLIC ACID;DU-6856;CHEMBL607160;DTXSID801101677;AKOS015896860;AM85540;3-Quinolinecarboxylicacid,7-[(7S)-7-amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1S,2R)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-;CS-0164491;A899083;7-((S)-7-amino-5-azaspiro[2.4]heptan-5-yl)-8-chloro-6-fluoro-1-((1S,2R)-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid? (Sitafloxacin Impurity pound(c);7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1S,2R)-2-fluorocyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Chemical Property of 7-[(7s)-7-Amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1s,2r)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Chemical Property:

• Boiling Point: 629.221 °C at 760 mmHg
• Flash Point: 334.341 °C
• PSA: 88.56000
• Density: 1.637 g/cm³
• LogP: 3.46790
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 409.1004755
• Heavy Atom Count: 28
• Complexity: 761

Purity/Quality:

98% min ^*data from raw suppliers

SSR 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC12CN(CC2N)C3=C(C=C4C(=C3Cl)N(C=C(C4=O)C(=O)O)C5CC5F)F
• Isomeric SMILES: C1CC12CN(C[C@H]2N)C3=C(C=C4C(=C3Cl)N(C=C(C4=O)C(=O)O)[C@H]5C[C@H]5F)F
• Uses: DU 6856, is an isomer of Sitafloxacin (S490920), which is an antibacterial.

Technology Process of 7-[(7s)-7-Amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1s,2r)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

There total 66 articles about 7-[(7s)-7-Amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1s,2r)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic 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: 97.3%

C26H30ClF2N3O5 → sitafloxacin (127254-12-0,127199-06-8,127254-10-8,127254-11-9,155421-11-7,163157-04-8,167355-47-7,273401-03-9)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 20 - 25 ℃; Cooling with ice;

Reference yield: 97.0%

7-[7-(s)-tert-butoxycarbonylamino-5-azaspiro[2,4]-hept-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluoro-1-cyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid → sitafloxacin (127254-12-0,127199-06-8,127254-10-8,127254-11-9,155421-11-7,163157-04-8,167355-47-7,273401-03-9)

Guidance literature:

With hydrogenchloride; In dichloromethane; water; at 0 - 30 ℃; for 1h; Solvent;

Reference yield: 87.0%

C20H17BClF2N3O4 → sitafloxacin (127254-12-0,127199-06-8,127254-10-8,127254-11-9,155421-11-7,163157-04-8,167355-47-7,273401-03-9)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 0.833333h; Cooling with ice;

DOI:10.14233/ajchem.2014.17864

upstream raw materials:

(7S)-5-azaspiro[2.4]heptan-7-ylcarbamic acid tert-butyl ester

7-(S)-amino-5-<1(R)-phenylethyl>-5-azaspiro<2.4>heptane

7-(S)-amino-5-<1(R)-phenylethyl>-4-oxo-5-azaspiro<2.4>heptane

7(S)-<(tert-butoxycarbonyl)amino>-5-<1(R)-phenylethyl>-5-azaspiro<2.4>heptane

Refernces

• 1、 -. "Method for preparing sitafloxacin". Paragraph 0022; 0023; 0026; 0029. . Retrieved 2017/06/28.
• 2、 -. "A Sitafloxacine intermediate, Sitafloxacine preparation method and Sitafloxacine pharmaceutical composition". Paragraph 0024; 0060-0061. . Retrieved 2017/01/19.