Ethylene Glycol → HCID 53375922, compound

HRID 898111Notes

Reaction equation

HRID 898111 reaction equation
CS(C)=O.[CH2:5]([OH:8])[CH2:6][OH:7].CC([O-])(C)C.[K+].Cl[C:16]1[CH:25]=[C:24]2[C:19]([C:20](=[O:32])[C:21]([C:29]([OH:31])=[O:30])=[CH:22][N:23]2[CH:26]2[CH2:28][CH2:27]2)=[CH:18][C:17]=1[F:33]>O>[CH:26]1([N:23]2[C:24]3[C:19](=[CH:18][C:17]([F:33])=[C:16]([O:7][CH2:6][CH2:5][OH:8])[CH:25]=3)[C:20](=[O:32])[C:21]([C:29]([OH:31])=[O:30])=[CH:22]2)[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 679Dimethyl SulfoxideHCID 483180Fluoroquinolonic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 53375922HCID 53375922, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of DMSO (5 ml) and ethyleneglycol (6 ml), KOtBu (1.6 g, 14.23 mmol) was added portionwise over 10 min, and then heated to 90° C. To the mixture, 7chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (1.0 g) was added portionwise over 20 min, the temperature was increased to 105° C. and the mixture was stirred for 6 h. Water (30 ml) was added to the reaction solution and the pH of the solution was adjusted to pH=5. The resulting solution was left in the refrigerator overnight. The precipitate obtained was filtered, washed with cold water, and dried affording a 2:1 mixture of Intermediate 26A and Intermediate 26B (1.0 g).

Workup

  1. additionwas added portionwise over 10 min
  2. temperaturethe temperature was increased to 105° C.
  3. waitThe resulting solution was left in the refrigerator overnight
  4. customThe precipitate obtained
  5. filtrationwas filtered
  6. washwashed with cold water
  7. customdried
  8. customaffording

Sources & evidence

ORD record
ord-952735a199db4c33b67c6038056928de
Source dataset
uspto-grants-2008_04
Patent number
US07351696B2

Reaction notes

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