Triethylamine → 1-Cyclopropyl-7-(3-methylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid boron difluoride

HRID 505864Notes

Reaction equation

HRID 505864 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[C:13]([O:14][CH3:15])=[C:12]3[N:16]([CH:24]4[CH2:26][CH2:25]4)[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[C:19](=[O:20])[C:11]3=[CH:10][C:9]=2[F:27])[CH2:3]1.Cl.[B:29]([F:31])[F:30].C1(N2C3C(=CC(F)=C(F)C=3OC)C(=O)C(C(O)=O)=C2)CC1.CC1CNCCN1.C(N(CC)CC)C>CS(C)=O.C(O)C>[B:29]([F:31])[F:30].[CH:24]1([N:16]2[C:12]3[C:11](=[CH:10][C:9]([F:27])=[C:8]([N:4]4[CH2:5][CH2:6][NH:7][CH:2]([CH3:1])[CH2:3]4)[C:13]=3[O:14][CH3:15])[C:19](=[O:20])[C:18]([C:21]([OH:23])=[O:22])=[CH:17]2)[CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 660572-MethylpiperazineHCID 17956339Gatifloxacin hydrochloride2×HCID 86585298Difluoroborane 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate

Product 1

HCID 866203141-Cyclopropyl-7-(3-methylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid boron difluoride

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

U.S. Pat. No. 4,997,943 discloses the Gatifloxacin hydrochloride salts, describes the process for preparation of Gatifloxacin hydrochloride by reaction of 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid boron difluoride chelate with 2-methyl piperazine in DMSO, isolating the intermediate 1-Cyclopropyl-7-(3-methylpiperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid boron difluoride chelate which on treatment with triethylamine in aqueous ethanol followed by isolation of the crystals and treating with hydrochloric acid in ethanol.

Sources & evidence

ORD record
ord-140f870617f44417a0dfacf05cf86bde
Source dataset
uspto-grants-2010_08
Patent number
US07781585B2

Reaction notes

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