Methanol → HCID 22903657, compound

HRID 1489169Notes

Reaction equation

HRID 1489169 reaction equation
[NH2:1][CH2:2][C:3]1([CH2:28][F:29])[CH2:7][CH2:6][N:5]([C:8]2[C:17]([O:18][CH3:19])=[C:16]3[C:11]([C:12](=[O:26])[C:13]([C:23]([OH:25])=[O:24])=[CH:14][N:15]3[CH:20]3[CH2:22][CH2:21]3)=[CH:10][C:9]=2[F:27])[CH2:4]1.S(Cl)(Cl)=O.[CH3:34]O>>[NH2:1][CH2:2][C:3]1([CH2:28][F:29])[CH2:7][CH2:6][N:5]([C:8]2[C:17]([O:18][CH3:19])=[C:16]3[C:11]([C:12](=[O:26])[C:13]([C:23]([O:25][CH3:34])=[O:24])=[CH:14][N:15]3[CH:20]3[CH2:22][CH2:21]3)=[CH:10][C:9]=2[F:27])[CH2:4]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 22277663HCID 22277663, compound

Product 1

HCID 22903657HCID 22903657, compound

Procedure

7-(3-Aminomethyl-3-fluoromethylpyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (8.9 g) obtained in Example 1 was suspended in methanol (100 ml) and thionyl chloride (3.2 ml) was dropwise added with stirring under ice-cooling. After the dropwise addition, the mixture was refluxed overnight. Methanol and excess thionyl chloride were distilled away under reduced pressure. The residue was dissolved in water and the solution was made alkaline with potassium carbonate. The mixture was extracted twice with chloroform, dried and concentrated to dryness to give 9.8 g of the object compound, melting point 143°-145° C.

Workup

  1. temperaturecooling
  2. additionAfter the dropwise addition
  3. temperaturethe mixture was refluxed overnight
  4. distillationMethanol and excess thionyl chloride were distilled away under reduced pressure
  5. dissolutionThe residue was dissolved in water
  6. extractionThe mixture was extracted twice with chloroform
  7. customdried
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-264b7467808f4ba9ae7810b4932ca9a7
Source dataset
uspto-grants-1997_10
Patent number
US05677316

Reaction notes

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