Water → Ethyl 6-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate

HRID 600873Notes

Reaction equation

HRID 600873 reaction equation
F[C:2]1[C:3]([N+:25]([O-:27])=[O:26])=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[N:8]([C@@H:15]1[CH2:17][C@@H:16]1[F:18])[CH:7]=[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]2=[O:24].O.[NH3:29].O.C(Cl)(Cl)Cl>CN(C)C=O>[NH2:29][C:2]1[C:3]([N+:25]([O-:27])=[O:26])=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[N:8]([C@@H:15]1[CH2:17][C@@H:16]1[F:18])[CH:7]=[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:5]2=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 12896473Azane;hydrateHCID 67272160Ethyl 6,7-difluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate

Product 1

HCID 67271603Ethyl 6-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 6,7-difluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (13.96 g, 36.14 mmol) was dissolved in dimethyl formamide (180 ml), and 28% ammonia water (60 ml) was added dropwise in while stirring and cooling with ice. After stirring the reaction solution at room temperature for 64 hours, water (100 ml) was added to the reaction solution and then concentrated under a reduced pressure. The water-containing residue obtained was then subjected to extraction with ethyl acetate (100 ml×3), and the organic layers were then combined, washed with water (150 ml×3) and saturated saline solution (200 ml) in that order, and then dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated under a reduced pressure, the residue obtained was applied to a silica gel chromatography, and 8.92 g (64%) of the title compound was obtained in the form of a pale red, oily substance from a chloroform:methanol=30:1 eluate.

Workup

  1. temperaturecooling with ice
  2. stirringAfter stirring the reaction solution at room temperature for 64 hours
  3. concentrationconcentrated under a reduced pressure
  4. additionThe water-containing residue
  5. customobtained
  6. extractionwas then subjected to extraction with ethyl acetate (100 ml×3)
  7. washwashed with water (150 ml×3) and saturated saline solution (200 ml) in that order
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtering
  10. concentrationthe filtrate was concentrated under a reduced pressure
  11. customthe residue obtained

Sources & evidence

ORD record
ord-6f23dd2f5bb44fc4be56f4bce738a77a
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

Loading…