Dimethyl Sulfoxide → HCID 73530187, compound

HRID 1197494Notes

Reaction equation

HRID 1197494 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[OH:22][N:23]=[C:24]1[CH2:28][CH2:27][NH:26][CH2:25]1.FC(F)(F)C([O-])=O.CS(C)=O>C(O)(C)C>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([F:17])[C:10]([F:16])=[C:11]([N:26]4[CH2:27][CH2:28][C:24](=[N:23][OH:22])[CH2:25]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 138255151-Cyclopropyl-5,6,7,8-tetrafluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acidHCID 86747461HCID 86747461, compound

Product 1

HCID 73530187HCID 73530187, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The reaction was conducted at room temperature for 3 hours in the same manner as in Example 3 except that 300 mg (1 mmol) of 1-cyclopropyl-5,6,7,8-tetrafluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 535 mg (2.5 mmol) of 3-hydroxyiminopyrrolidine-trifluoroacetate were used as starting materials and 5 ml of dimethyl sulfoxide was used as the solvent for reaction. 7 ml of isopropanol was added to the reaction mixture, and the precipitate thereby formed was collected by filtration and recrystallized from a mixture of 6 ml of dimethyl sulfoxide and 6 ml of isopropanol to give 170 mg of the desired product as pale yellow powder.

Workup

  1. customwas used as the solvent for reaction
  2. customthe precipitate thereby formed
  3. filtrationwas collected by filtration
  4. customrecrystallized from a mixture of 6 ml of dimethyl sulfoxide and 6 ml of isopropanol

Sources & evidence

ORD record
ord-8e5da032f5764031928cc8524c2baf3e
Source dataset
uspto-grants-1994_01
Patent number
US05276041

Reaction notes

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