Norfloxacin → HCID 474727, compound

HRID 2297559Notes

Reaction equation

HRID 2297559 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]([F: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]([F: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

3

Reactant 2

HCID 4539NorfloxacinHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 474727HCID 474727, compound

Procedure

1-Ethyl-6-fluoro-7-{4-[2-(4-fluorophenyl)-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′-fluoroaceto-phenone(0.40 g, 1.86 mmole) by a method similar to that described for Example 4 (61% yield). Mp: 208° C. (dec). 1H NMR (DMSO-d6) δ 1.41 (t, 3H, J=7.0), 2.73 and 3.3 (two m, 8H), 3.94 (s, 2H), 4.58 (q, 2 H. J=7.0), 7.18 (d, 1H, J=7.0), 7.36 (m, 2H), 7.90 (d, 1H, J=13.2), 8.11 (m, 2H), 8.94 (s, 1H), 15.30 (br s, 1H). Anal. Calcd. for C24H23F2N3O4: C, 63.29; H, 5.09; N, 9.23. Found: C, 62.96; H, 5.19; N, 9.16.

Sources & evidence

ORD record
ord-f022c148c1e3415190714b76c9e15a99
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

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