2-Bromo-1-(4-fluorophenyl)ethan-1-one → HCID 10950831, compound

HRID 2297563Notes

Reaction equation

HRID 2297563 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:20])=[C:10]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:11]=2[F:13])[C:6](=[O:21])[C:5]([C:22]([OH:24])=[O:23])=[CH:4]1)[CH3:2].Br[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)=[O:28]>>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:20])=[C:10]([N:14]3[CH2:15][CH2:16][N:17]([CH2:26][C:27]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)=[O:28])[CH2:18][CH2:19]3)[C:11]=2[F:13])[C:6](=[O:21])[C:5]([C:22]([OH:24])=[O:23])=[CH:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 1135233-Quinolinecarboxylic acid, 1,4-dihydro-6,8-difluoro-1-ethyl-4-oxo-7-(1-piperazinyl)-

Product 1

HCID 10950831HCID 10950831, compound

Procedure

1-Ethyl-6,8-difluoro-7-{4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid was prepared from 1-ethyl-6,8-difluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-quinoline-3-carboxylic acid (0.50 g, 1.48 mmole) and 2-bromo-4′-fluoroacetophenone (0.40 g, 1.86 mmole) by a method similar to that described for Example 4 (64% yield). Mp: 170° C. (dec). 1H NMR (DMSO-d6) δ 1.44 (t, 3H, J=7.0), 2.70 and 3.3 (two m, 8H), 3.94 (s, 2H), 4.58 (q, 2H, J=7.0), 7.37 (n, 2H), 7.90 (d, 1H, J=11.8), 8.11 (m, 2H), 8.92 (s, 1H), 14.92 (br s, 1H). Anal. Calcd. for C24H22F3N3O4•0.5 H2O: C, 59.75; H, 4.80; N, 8.71. Found: C, 59.39; H, 4.66; N, 8.62.

Sources & evidence

ORD record
ord-1e990ce2434d469b9440a39038b7880f
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

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