1,1'-Carbonyldiimidazole → HCID 14576671, compound

HRID 1607301Notes

Reaction equation

HRID 1607301 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=O.[F:13][C:14]1[CH:15]=[C:16]2[C:21](=[C:22]([OH:25])C=1F)[N:20]([NH:26][CH3:27])[CH:19]=[C:18]([C:28]([OH:30])=[O:29])[C:17]2=[O:31]>CN(C)C=O>[F:13][C:14]1[CH:15]=[C:16]2[C:21](=[C:22]([OH:25])[C:1]=1[N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[N:20]([NH:26][CH3:27])[CH:19]=[C:18]([C:28]([OH:30])=[O:29])[C:17]2=[O:31]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 14576603Marbofloxacin EP Impurity A

Product 1

HCID 14576671HCID 14576671, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Carbonyldiimidazole (32 mg) was added to a stirred solution of 6,7-difluoro-8-hydroxy-1-(methylamino)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (50 mg) obtained in Reference example (i) in dry dimethylformamide (2 ml). Stirring was continued at room temperature for 2 hours and then at 80° C. for 5 hours. The solvent was removed under reduced pressure and the residue was suspended in water and the pH was adjusted to pH 5 with acetic acid. The precipitate which separated out was filtered and washed with methanol to give 35 mg of 6-fluoro-8-hydroxy-7-(1-imidazolyl)-1-(methylamino)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid as pale yellow powder, FAB-MS m/z 319 (MH+); 1H-NMR (d6 -DMSO) δ: 2.82 (3H, s), 7.10 (1H, d, J=10.7 Hz), 7.61 (1H, d), 7.75 (1H, d), 8.62 (1H, s), 8.92 (1H, s), 15.33 (1H, br.s)

Workup

  1. waitat 80° C. for 5 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe precipitate which separated out
  4. filtrationwas filtered
  5. washwashed with methanol

Sources & evidence

ORD record
ord-547f1b08b5374f53b3c9603f349b7286
Source dataset
uspto-grants-1989_09
Patent number
US04864023

Reaction notes

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