Potassium Bicarbonate → 8-Cyano-1-cyclopropyl-7-[(1S,6S)-2-(5methyl-2-oxo-1,3-dioxol-4-yl)methyl-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 651280Notes

Reaction equation

HRID 651280 reaction equation
[C:1]([C:3]1[C:4]([N:21]2[CH2:29][C@@H:28]3[C@@H:23]([CH2:24][CH2:25][CH2:26][NH:27]3)[CH2:22]2)=[C:5]([F:20])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([OH:18])=[O:17])[C:8]2=[O:19])#[N:2].Br[CH2:31][C:32]1[O:33][C:34](=[O:38])[O:35][C:36]=1[CH3:37].C(=O)(O)[O-].[K+]>CN(C)C=O>[C:1]([C:3]1[C:4]([N:21]2[CH2:29][C@@H:28]3[C@@H:23]([CH2:24][CH2:25][CH2:26][N:27]3[CH2:31][C:32]3[O:33][C:34](=[O:38])[O:35][C:36]=3[CH3:37])[CH2:22]2)=[C:5]([F:20])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:14][CH2:15]1)[CH:10]=[C:9]([C:16]([OH:18])=[O:17])[C:8]2=[O:19])#[N:2]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 9802884PradofloxacinHCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

Product 1

HCID 701084258-Cyano-1-cyclopropyl-7-[(1S,6S)-2-(5methyl-2-oxo-1,3-dioxol-4-yl)methyl-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.25 mmol) of 8-cyano-1-cyclopropyl-7-((1S,6S)-2,8-diazabicyclo[4.3.0]-nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 59 mg (0.30 mmol) of 4-bromomethyl-5-methyl-1,3-dioxol-2-one and 30 mg of potassium bicarbonate are heated at 140° C. in 2 ml of dimethylformamide for 30 minutes. The reaction solution is concentrated in vacuo, the residue is taken up in methylene chloride and the mixture is washed with water. The organic phase is dried over magnesium sulfate and concentrated in vacuo. The resulting residue is stirred with water, filtered off with suction and dried.

Workup

  1. concentrationThe reaction solution is concentrated in vacuo
  2. washthe mixture is washed with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationfiltered off with suction
  6. customdried

Sources & evidence

ORD record
ord-b83e3be2654649b0a695f16018a44d6b
Source dataset
uspto-grants-2001_08
Patent number
US06278013B1

Reaction notes

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