Water → HCID 13850791, compound

HRID 1382213Notes

Reaction equation

HRID 1382213 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[CH2:3][CH2:2]1.N12CCN(CC1)CC2.Cl[C:19]1[CH:28]=[C:27]2[C:22]([C:23](=[O:35])[C:24]([C:32]([OH:34])=[O:33])=[CH:25][N:26]2[CH:29]2[CH2:31][CH2:30]2)=[CH:21][C:20]=1[F:36].O>CS(C)=O>[CH:29]1([N:26]2[C:27]3[C:22](=[CH:21][C:20]([F:36])=[C:19]([N:7]4[CH2:8][CH2:9][N:4]([CH:1]5[CH2:3][CH2:2]5)[CH2:5][CH2:6]4)[CH:28]=3)[C:23](=[O:35])[C:24]([C:32]([OH:34])=[O:33])=[CH:25]2)[CH2:30][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 483180Fluoroquinolonic acidHCID 47420041-Cyclopropylpiperazine

Product 1

HCID 13850791HCID 13850791, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.3 g of 1-cyclopropylpiperazine and 2.2 g (20 mmol) of 1,4-diazabicyclo[2.2.2]octane are added to 2.8 g (10 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 25 ml of dimethyl sulphoxide, and the mixture is heated at 140° for 5 hours. 40 ml of water are added to the suspension and the precipitate is filtered off with suction, washed with water and boiled up with 20 ml of methanol. 1.2 g of 1-cyclopropyl-7-(4-cyclopropyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of melting point 226°-229° (with decomposition) are obtained.

Workup

  1. temperaturethe mixture is heated at 140° for 5 hours
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with water

Sources & evidence

ORD record
ord-7275365cd9f549d19c5972671276cdb1
Source dataset
uspto-grants-1989_02
Patent number
US04806539

Reaction notes

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