Reaction #1406

ord-b9c49b6d642f487a8b46731f4e1e7af0

Reaction equation

O=C(O)c1cn(C2CC2)c2c(Cl)c(N3CC[C@H](N=Cc4cccc([N+](=O)[O-])c4)C3)c(F)cc2c1=O
8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-7-[(S)-3-(3-nitrobenzylideneamino)-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid
O=Cc1cccc([N+](=O)[O-])c1
3-nitrobenzaldehyde
N[C@H]1CCNC1
(S)-3-aminopyrrolidine
O=C(O)c1cn(C2CC2)c2c(Cl)c(F)c(F)cc2c1=O
8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
→
Cl.N[C@H]1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(C4CC4)c3c2Cl)C1
7-[(S)-3-amino-1-pyrrolidinyl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride

Reactants

O=C(O)c1cn(C2CC2)c2c(Cl)c(N3CC[C@H](N=Cc4cccc([N+](=O)[O-])c4)C3)c(F)cc2c1=O
8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-7-[(S)-3-(3-nitrobenzylideneamino)-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid
O=Cc1cccc([N+](=O)[O-])c1
3-nitrobenzaldehyde
N[C@H]1CCNC1
(S)-3-aminopyrrolidine
O=C(O)c1cn(C2CC2)c2c(Cl)c(F)c(F)cc2c1=O
8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

If, for example, the reaction mixture of 3-nitrobenzaldehyde and (S)-3-aminopyrrolidine is reacted with 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in a one-pot reaction, the course of the reaction via the intermediately formed 8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-7-[(S)-3-(3-nitrobenzylideneamino)-1-pyrrolidinyl]-4-oxo-3-quinolinecarboxylic acid to give 7-[(S)-3-amino-1-pyrrolidinyl]-8-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride can be represented by the following equation: ##STR19##

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723627uspto-grants-1998_03