146836-84-2

Usage

InChI:InChI=1/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16+

Upstream product

• 75-75-2 methanesulfonic acid 
• 210236-57-0 7-((1R,5S,6R)-6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 232598-25-3 (1α, 5α, 6α)-7-(6-acetamido-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester 
• 71-36-3 butan-1-ol 
• 288628-57-9 (1α,5α,6α)-6-Benzylideneamino-3-azabicyclo[3.1.0]hexane 
• 185693-08-7 (1α,5α,6α)-6-amino-3-azabicyclo[3.1.0]hexane 
• 134575-17-0 tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate 
• 151860-17-2 (1α,5α,6α)-3-N-benzyl-6-amino-3-aza-bicyclo[3.1.0]hexane 
• 100491-29-0 ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 
• 134575-66-9 7-([1α,5α,6α]-6-tert-Butoxycarbonylamino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid,ethyl ester 
• 288628-59-1 Ethyl (1α,5α,6α)-7-(6-benzylideneamino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 
• 171176-56-0 Ethyl (1α,5α,6α)-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate 
• 210165-72-3 7-((1R,5S,6R)-6-Dibenzylamino-3-aza-bicyclo[3.1.0]hex-3-yl)-1-(2,4-difluoro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester 
• 210165-62-1 Dibenzyl-((1R,5S,6S)-3-benzyl-6-methoxy-3-aza-bicyclo[3.1.0]hex-6-yl)-amine 

Relevant academic research and scientific papers

Process for preparing trovafloxacin acid salts

Trovafloxacin acid salts are prepared via the hydrolysis of imine intermediates using mineral acid including, but not limited to, methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, nitric acid, sulfuric acid, phosphoric acid, hydrochloric ac

Process for preparing naphthyridones and intermediates

A process for preparing a naphthyridone carboxylic acid and its derivatives makes use of side chain intermediates of formulae I and IV herein.

Synthesis of trovafloxacin using various (1α,5α,6α)-3-azabicyclo[3.1.0]hexane derivatives

Trovafloxacin, a novel broad spectrum antibacterial, contains the unusual (1α,5α,6α)-3-azabicyclo[3.1.0]hexane ring system. The prototype of the industrial synthesis of this ring system and possible mechanistic pathways to exclusive formation of the exo or 6α-nitro derivative 4 are described, which leads to the key 6a-nitro-3-azabicyclo[3.1.0]hexane intermediate 10. The synthesis of 6a-amino-3-azabicyclo[3.1.0]hexane 16 and useful protected cxo 6-amino derivatives 15 and 17 follows from 10. These can be coupled with the 7-chloronaphthyridone 18 to yield protected trovafloxacin compounds 20-22 in good yield. The ethyl ester of trovafloxacin 21 can also be accessed from the product of coupling 19, derived from 18 and the exo 6-nitro-3-azabicyclo[3.1.0]hexane compound 12. Removal of protecting groups from 20-22 with methanesulfonic acid yields trovafloxacin mesylate from which trovafloxacin zwitterion 1 can be liberated with base treatment. Zwitterion l can also be prepared directly from 16 tosylate salt and naphthyridone-2-carboxylic acid 26. The Royal Society of Chemistry 2000.

Diastereoselective syntheses of N-protected derivatives of 1α,5α,6β- 6-amino-3-azabicyclo[3.1.0]hexane; a route to trovafloxacin 6β-diastereomer

N-Protected derivatives 12, 13 and 17 of 1α,5α,6β-6-amino-3- azabicyclo[3.1.0]hexane 5 were synthesized via chloroenamines 6a or 6b. The specific N-protection was realized either by using a chloroenamine 6b with different protecting groups or by selective removal of identical protecting groups at the bicyclic target molecule 7. Dibenzylamino compound 13 allowed the preparation of naphthyridine derivative 25 which represents the 6β- diastereomer of trovafloxacin mesylate, a potent Gyrase inhibitor.