Bromomethyl 4-methoxyphenyl ketone → HCID 482679, compound

HRID 2297555Notes

Reaction equation

HRID 2297555 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]([O:35][CH3:36])=[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]([O:35][CH3:36])=[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 4965Bromomethyl 4-methoxyphenyl ketoneHCID 1135233-Quinolinecarboxylic acid, 1,4-dihydro-6,8-difluoro-1-ethyl-4-oxo-7-(1-piperazinyl)-

Product 1

HCID 482679HCID 482679, compound

Procedure

1-Ethyl-6,8-difluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was prepared from 1-ethyl-6,8-difluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydroquinoline-3-carboxylic acid (0.50 g, 1.48 mmole) and 2-bromo-4′-methoxy-acetophenone (0.43 g, 1.86 mmole) by a method similar to that described for Example 4 (63% yield). Mp: 190° C. (dec). 1H NMR (DMSO-d6) δ 1.44 (t, 3H, J=7.0), 2.69 and 3.24 (two m, 8H), 3.84 (s, 3H), 3.87 (s, 2H), 4.58 (q, 2H, J=7.0), 7.05 (m, 2H), 7.85 (d, 1H), J=12.0), 8.01 (m, 2H), 8.92 (s, 1H), 14.92 (br s, 1H). Anal. Calcd. for C25H25F2N3O5•0.25 H2O: C, 61.28; H, 5.25; N, 8.58. Found: C, 61.25; H, 5.23; N, 8.67.

Sources & evidence

ORD record
ord-99cbfd33c95049ccb5c8e69fd1bfc085
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

Loading…