Bromomethyl 4-methoxyphenyl ketone → HCID 482688, compound

HRID 2297557Notes

Reaction equation

HRID 2297557 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:26])=[C:17]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[CH:18]=3)[C:13](=[O:27])[C:12]([C:28]([OH:30])=[O:29])=[CH:11]2)=[C:6]([F:31])[CH:5]=1)([O-:3])=[O:2].Br[CH2:33][C:34]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[O:35].C(=O)(O)[O-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:26])=[C:17]([N:20]4[CH2:25][CH2:24][N:23]([CH2:33][C:34]([C:36]5[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=5)=[O:35])[CH2:22][CH2:21]4)[CH:18]=3)[C:13](=[O:27])[C:12]([C:28]([OH:30])=[O:29])=[CH:11]2)=[C:6]([F:31])[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 482686HCID 482686, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 482688HCID 482688, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 1-(4-nitro-2-fluorophenyl)-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (0.43 g, 1 mmol) in DMF (15 ml) was added 2-bromo-4′-methoxyacetophenone (0.29 g, 1.28 mmol) and sodium bicarbonate (0.08 g, 1 mmol). The reaction mixture was stirred for 24 hr at room temperature. After removing the solvent, the residue was taken up by CH2Cl2, solution, and after washed with water and dried with Na2SO4, was evaporated to dryness. Crystallization of the solid residue from CH2Cl2/methanol (10:1) afforded the desired 1-(4-nitro-2-fluorophenyl)-6-fluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (0.37 g, 86%). Mp: 136° C. (dec). 1H NMR (DMSO-d6) δ 2.63 and 3.10 (two m, 8),3.81-3.83 (m, 5H) 6.40 (d, 1H, J=6.8), 7.01 (d, 2H, J=9.0), 7.94-8.03 (m, 3H), 8.17-8.56 (m, 3H), 8.93 (s, 1H), 14.88 (br s, 1H). Anal. Calcd. for C29H24F2N4O7•H2O: C, 58.39; H, 4.39; N, 9.39. Found: C, 58.75; H, 4.42; N, 9.20.

Workup

  1. customAfter removing the solvent
  2. washafter washed with water
  3. dry with materialdried with Na2SO4
  4. customwas evaporated to dryness
  5. customCrystallization of the solid residue from CH2Cl2/methanol (10:1)

Sources & evidence

ORD record
ord-6731aff743c14df79622deaf307e05d7
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

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