HCID 70395271, compound → HCID 14052589, compound

HRID 1722304Notes

Reaction equation

HRID 1722304 reaction equation
[ClH:1].[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:28])=[C:12]([N:16]4[CH2:20][CH2:19][CH:18]([CH2:21][N:22](CC)[C:23](=O)[CH3:24])[CH2:17]4)[C:13]=3[CH3:15])[C:8](=[O:29])[C:7]([C:30]([OH:32])=[O:31])=[CH:6]2)[CH2:4][CH2:3]1>[OH-].[Na+]>[ClH:1].[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][C:11]([F:28])=[C:12]([N:16]4[CH2:20][CH2:19][CH:18]([CH2:21][NH:22][CH2:23][CH3:24])[CH2:17]4)[C:13]=3[CH3:15])[C:8](=[O:29])[C:7]([C:30]([OH:32])=[O:31])=[CH:6]2)[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 70395271HCID 70395271, compound

Product 1

HCID 14052589HCID 14052589, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To 1-cyclopropyl-7-[3-(N-ethylacetamido)methyl-1-pyrrolidinyl]-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride (0.22 g) is added 5% aqueous sodium hydroxide (10 ml), and the mixture is refluxed for 24 hours. After cooling, the insoluble materials are filtered off, and the filtrate is acidified with conc. hydrochloric acid. The mixture is extracted with dichloromethane, and the aqueous layer is made alkaline with aqueous sodium hydroxide, and thereto is added t-butoxycarboxylic anhydride (200 mg). The mixture is stirred at room temperature for 30 minutes. The reaction mixture is acidified with 10% hydrochloric acid and is extracted with dichloromethane. After removing the solvent by concentration, to the resulting residue are added 10% hydrochloric acid (5 ml) and methanol (10 ml), and the mixture is heated at 70° C. for 30 minutes. After concentrating, the resulting residue is recrystallized from methanol-acetonitrile to give 1-cyclopropyl-7-(3-ethylaminomethyl-1-pyrrolidinyl)-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride (30 mg), as yellow crystals, m.p. 267°-271° C.

Workup

  1. temperaturethe mixture is refluxed for 24 hours
  2. temperatureAfter cooling
  3. filtrationthe insoluble materials are filtered off
  4. extractionThe mixture is extracted with dichloromethane
  5. additionis added t-butoxycarboxylic anhydride (200 mg)
  6. extractionis extracted with dichloromethane
  7. customAfter removing the solvent
  8. concentrationby concentration
  9. additionto the resulting residue are added 10% hydrochloric acid (5 ml) and methanol (10 ml)
  10. temperaturethe mixture is heated at 70° C. for 30 minutes
  11. concentrationAfter concentrating
  12. customthe resulting residue is recrystallized from methanol-acetonitrile

Sources & evidence

ORD record
ord-77ed7760287a4661b65b01933692008d
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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