HCID 482688, compound → HCID 482690, compound

HRID 2297565Notes

Reaction equation

HRID 2297565 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[C:20]2[C:15](=[CH:16][C:17]([F:38])=[C:18]([N:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]([C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)=[O:29])[CH2:23][CH2:22]3)[CH:19]=2)[C:14](=[O:39])[C:13]([C:40]([OH:42])=[O:41])=[CH:12]1>C(O)C.[H][H].[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[C:20]3[C:15](=[CH:16][C:17]([F:38])=[C:18]([N:21]4[CH2:22][CH2:23][N:24]([CH2:27][C:28]([C:30]5[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=5)=[O:29])[CH2:25][CH2:26]4)[CH:19]=3)[C:14](=[O:39])[C:13]([C:40]([OH:42])=[O:41])=[CH:12]2)=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 1

HCID 482688HCID 482688, compound

Product 1

HCID 482690HCID 482690, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a suspension of the 1-(2-fluoro-4-nitrophenyl)-6-fluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid [example 8] (0.58 g, 1 mmol) in ethanol (20 ml) was hydrogenated overnight in hydrogen in the presence of 10% Pd/C (25 mg) at room temperature. The reaction mixture was filtered and the filtrate was evaporated in vacuo to give a solid, the resulting solid was recrystallized from ethanol to afford 1-(4-amino-2-fluorophenyl)-6-fluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (0.28 g, 51%). Mp: 143° C. (dec). 1H NMR (DMSO-d6) δ 2.66 and 3.09 (two m, 8H), 3.85-3.84 (m, 5H), 6.05 (s, 2H), 6.47 (d, 1H, J=7.2), 6.58 (m, 2H), 7.02 (m, 2H), 7.36 (m, 1H), 7.97 (m, 3H), 8.62 (s, 1H), 15.06 (br s, 1H). Anal. Calcd. for C29H26F2N4O5•1.0 H2O: C, 61.48; H, 4.98; N, 9.89. Found: C, 61.81; H, 4.85; N, 9.81.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customto give a solid
  4. customthe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-d5c1a1530108494e96eab319dd55e6f5
Source dataset
uspto-grants-2002_12
Patent number
US06492373B2

Reaction notes

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