Hydroxyamine hydrochloride → HCID 86585218, compound

HRID 2297560Notes

Reaction equation

[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:29])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[O:21])[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:30])[C:5]([C:31]([OH:33])=[O:32])=[CH:4]1)[CH3:2].Cl.[NH2:35]O>>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:29])=[C:10]([N:13]3[CH2:14][CH2:15][N:16]([C:19](=[NH:35])[CH:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[OH:21])[CH2:17][CH2:18]3)[CH:11]=2)[C:6](=[O:30])[C:5]([C:31]([OH:33])=[O:32])=[CH:4]1)[CH3:2]

Participants

Reactant 2

HCID 443297Hydroxyamine hydrochloride

HCID 474727HCID 474727, compound

Product 1

HCID 86585218HCID 86585218, compound

Procedure

1-Ethyl-6-fluoro-7-{4-[2-(4-fluorophenyl)-2-hydroxy-iminoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid was prepared from 1-ethyl-6-fluoro-7-{4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (0.23 g, 0.5 mmole) and hydroxylamine hydrochloride (0.07 g, 1 mmol) by a method similar to that described for Example 3 (66% yield). 1H NMR (DMSO-d6): δ 1.39 (t, 3H, J=7.2), 2.62 and 3.25 (two m, 8H), 3.44 and 3.73 (two s, 2H), 4.57 (q, 2H, J=7.2), 7.15 (d, 1H, J=7.2), 7.42-7.83 (m, 4H),7.89 (d, 1H, J=13.3), 8.93 (s, 1H), 11.19 and 11.62 (two s, 1H), 15.23 (br s, 1H) Anal. Calcd. for C24H24F2N4O4•0.5 H2O: C, 60.12; H, 5.26; N, 11.68. Found: C, 60.01; H, 5.24; N, 11.60.

Sources & evidence

ORD record: ord-1b0629f6e96d461cbdb34cd815814418
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492373B2

Reaction notes

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