Dabco → Methyl 8-cyano-1-cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]nonan-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 651282Notes

Reaction equation

HRID 651282 reaction equation
[C:1]([C:3]1[C:4](Cl)=[C:5]([F:21])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:8]2=[O:20])#[N:2].[C@@H:23]12[CH2:31][NH:30][CH2:29][C@@H:28]1[CH2:27][CH2:26][CH2:25][NH:24]2.N12CCN(CC1)CC2>C(#N)C>[C:1]([C:3]1[C:4]([N:30]2[CH2:31][C@@H:23]3[C@@H:28]([CH2:27][CH2:26][CH2:25][NH:24]3)[CH2:29]2)=[C:5]([F:21])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:8]2=[O:20])#[N:2]

Participants

5

Reactant 3

HCID 9237DabcoHCID 10313138(1S,6S)-2,8-Diazabicyclo(4.3.0)nonaneHCID 18351232Methyl 8-cyano-1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 15347199Methyl 8-cyano-1-cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]nonan-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

200 mg (0.625 mmol) of methyl 8-cyano-1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 86 mg (0.683 mmol) of (1S,6S)-2,8-diazabicyclo[4.3.0]nonane and 150 mg (1.34 mmol) of 1,4-diazabicyclo[2.2.2]-octane are stirred in 6 ml of acetonitrile at room temperature for 48 hours. Thereafter, the mixture is evaporated and the residue is partitioned between 15 ml of chloroform and 20 ml of saturated sodium carbonate solution. The organic phase is separated off, the aqueous phase is extracted again with chloroform and, after drying with sodium sulfate, the combined extracts are evaporated. For purification, the residue is chromatographed over silica gel with ethyl acetate/ethanol/25% strength aqueous ammonia solution.

Workup

  1. customThereafter, the mixture is evaporated
  2. customthe residue is partitioned between 15 ml of chloroform and 20 ml of saturated sodium carbonate solution
  3. customThe organic phase is separated off
  4. extractionthe aqueous phase is extracted again with chloroform
  5. dry with materialafter drying with sodium sulfate
  6. customthe combined extracts are evaporated
  7. customFor purification
  8. customthe residue is chromatographed over silica gel with ethyl acetate/ethanol/25% strength aqueous ammonia solution

Sources & evidence

ORD record
ord-54db9c0c21304d0d8e3aff2fba0042cc
Source dataset
uspto-grants-2001_08
Patent number
US06278013B1

Reaction notes

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