Norfloxacin → HCID 474729, compound

HRID 2297553Notes

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]([O:34][CH3:35])=[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]([O:34][CH3:35])=[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 4965Bromomethyl 4-methoxyphenyl ketone

Product 1

HCID 474729HCID 474729, compound

Procedure

1-Ethyl-6-fluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was prepared from norfloxacin (0.50 g, 1.56 mmole) [H. Koga et. al., J. Med. Chem. , 23, 1358 (1980).] and 2-bromo-4′-methoxyacetophenone (0.43 g, 1.86 mmole) by a method similar to that described for Example 4 (75% yield). Mp: 202° C. (dec). 1H NMR (DMSO-d6) δ 1.41 (t, 3H, J=7.0), 2.73 and 3.3 (two m, 8H), 3.85 (s, 3H), 3.88 (s, 2H), 4.58 (q, 2H, J=7.0), 7.02-7.2 (m, 3H), 7.87 (d, 1H, J=13.8), 8.01 (m, 2H), 8.94 (s, 1H), 15.33 (br s, 1H). Anal. Calcd. for C25H26FN3O5: C, 64.23; H, 5.61; N, 8.99. Found: C, 63.88; H, 5.61; N, 8.94.

Sources & evidence

ORD record: ord-f1341dbec82349a1ab637ee30020bdff
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492373B2

Reaction notes

Loading…