Norfloxacin → HCID 482669, compound

HRID 2297561Notes

Reaction equation

[CH3:1][CH2:2][N:3]1[C:9]2[CH:10]=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[C:12]([F:14])=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1.Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=[O:27]>>[CH2:2]([N:3]1[C:9]2[C:8](=[CH:13][C:12]([F:14])=[C:11]([N:15]3[CH2:20][CH2:19][N:18]([CH2:25][C:26]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=4)=[O:27])[CH2:17][CH2:16]3)[CH:10]=2)[C:6](=[O:7])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:1]

Participants

Reactant 2

HCID 4539Norfloxacin

HCID 68303p-Chlorophenacyl bromide

Product 1

HCID 482669HCID 482669, compound

Procedure

1-Ethyl-6-fluoro-7-{4-[2-(4-chlorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid was prepared from norfloxacin (0.5 g, 1.56 mmole) and 2-bromo-4′-chloroaceto-phenone(0.43 g, 1.86 mmole) by a method similar to that described for Example 4 (67% yield). Mp: 207° C. (dec). 1H NMR (DMSO-d6) δ 1.41 (7, 3H, J=7.2), 2.73 and 3.29 (two m, 8H), 3.95 (s, 2H), 4.58 (q, 2H, J=7.2 7.19 (d, 1H, J=7.2), 7.59 and 8.02 (m, 4H), 7.92 (d, 1H, J=13.2), 8.95 (s, 1H), 15.41 (br s, 1H). Anal. Calcd. for C24H23ClFN3O4•0.25H2O: C, 60.51; H, 4.97; N, 8.82. Found: C, 60.49; H, 4.96; N, 8.82.

Sources & evidence

ORD record: ord-80343a4dde814298a129ae1cb14148b5
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492373B2

Reaction notes

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