HCID 474729, compound → HCID 482693, compound

HRID 2297556Notes

Reaction equation

HRID 2297556 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:30])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=O)[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:31])[C:5]([C:32]([OH:34])=[O:33])=[CH:4]1)[CH3:2].Cl.[CH3:36][O:37][NH2:38]>>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:30])=[C:10]([N:13]3[CH2:14][CH2:15][N:16]([CH2:19][C:20](=[N:38][O:37][CH3:36])[C:22]4[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)[CH2:17][CH2:18]3)[CH:11]=2)[C:6](=[O:31])[C:5]([C:32]([OH:34])=[O:33])=[CH:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 474729HCID 474729, compoundHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 482693HCID 482693, compound

Procedure

1-Ethyl-6-fluoro-7-{4-[2-methoxyimino-2-(4-methoxyphenyl)ethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was prepared from 1-ethyl-6-fluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (0.23 g, 0.5 mmol) and O-methylhydroxylamine hydrochloride (0.08 g, 1 mmol) by a method similar to that described for Example 3 (68% yield). Mp: 165° C. (dec). 1H NMR (DMSO-d6) δ 1.38 (t, 3H, J=7.0), 2.61 and 3.23 (two m, 8H), 3.69 and 3.79 (m, 6H), 3.89 (s, 2H), 4.54 (q, 2H, J=7.0), 6.93 (m, 2H), 7.13 (d, 1H, J=7.2), 7.73 (m, 2H), 7.89 (d, 1H, J=13.2), 8.90 (s, 1,H) 15.35 (br s, 1H). Anal. Calcd. for C26H29FN4O5H2O: C, 60.69; H, 6.07; N, 10.88. Found: C, 60.90; H, 5.77; N, 10.62.

Sources & evidence

ORD record
ord-e84450189278469bbf143d7e0256838b
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

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