Triethylamine → 6-Fluoro-1-(2,4-difluorophenyl)1,4-dihydro4-oxo-7-(5-benyl-2,5-diazabicyclo(2.2.1)-hept-2-yl)-quinoline-3-carboxylic acid

HRID 727938Notes

Reaction equation

HRID 727938 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:20]([OH:22])=[O:21])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:4][C:3]=1[F:24].FOBOF.Br.Br.[CH2:32]([N:39]1[CH2:44][CH:43]2[CH2:45][CH:40]1[CH2:41][NH:42]2)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(N(CC)CC)C>CS(C)=O>[F:24][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:42]1[CH2:41][CH:40]3[CH2:45][CH:43]1[CH2:44][N:39]3[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[N:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19])[CH:8]=[C:7]([C:20]([OH:22])=[O:21])[C:6]2=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11484989N-(2,4-difluorophenyl)-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acidHCID 166374642-Benzyl-2,5-diazabicyclo[2.2.1]heptane dihydrobromideHCID 178506430HCID 178506430, compound

Product 1

HCID 140148296-Fluoro-1-(2,4-difluorophenyl)1,4-dihydro4-oxo-7-(5-benyl-2,5-diazabicyclo(2.2.1)-hept-2-yl)-quinoline-3-carboxylic acidYield 39%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Analogous to example 6 but utilizing 5.56 g (13.85 m Mol) of the mixed anhydride of 7-chloro-6-fluoro-1-(2,4-difluorophenyl)1,4-dihydro-4-oxoquinoline-3-carboxylic acid and difluoroboronic acid, 5.82 g (16.62 m Mol) 2-benzyl-2,5-diazabicyclo(2.2.1)heptane dihydrobromide and 11.58 ml (83 m Mol)triethylamine in 50 ml dry DMSO yielded 2.73 g (39%) of the product, mp 233° C.-238° C. dec.

Sources & evidence

ORD record
ord-29cd10e371fc4cc594d944101c602c84
Source dataset
uspto-grants-1991_09
Patent number
US05045549

Reaction notes

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