Formic Acid → N-Methyl Gatifloxacin HCl

HRID 358862

반응식

HRID 358862 반응식
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:16]4[CH2:21][CH2:20][NH:19][CH:18]([CH3:22])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)[CH2:3][CH2:2]1.[ClH:28].[CH:29](O)=O>C=O>[ClH:28].[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:23])=[C:11]([N:16]4[CH2:21][CH2:20][N:19]([CH3:29])[CH:18]([CH3:22])[CH2:17]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:24])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2)[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 313Hydrochloric Acid2회HCID 5379Gatifloxacin

생성물 1

HCID 67925406N-Methyl Gatifloxacin HCl

시약·촉매·용매 1

HCID 712Formaldehyde용매

실험 절차

A solution of 1.5 g (0.004 mole) of 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (free form) (prepared as described in Example 22, but omitting the final reaction with hydrochloric acid) in a mixture of 75 ml of 90% aqueous formic acid and 45 ml of 37% aqueous formaldehyde was heated under reflux for 15 hours. 8 ml of concentrated hydrochloric acid were then added to the reaction mixture, and the solvent (formic acid, formalin and water) was then removed by evaporation under reduced pressure. Methanol was then added to the residue, and the resulting solution was filtered to remove insoluble material. The filtrate was evaporated to dryness under reduced pressure, and the residue was washed with ethanol to afford 1.35 g of 1-cyclopropyl-6-fluoro-8-methoxy-7-(3,4-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride as a colorless powder melting at 218°-221° C. (with decomposition).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. customthe solvent (formic acid, formalin and water) was then removed by evaporation under reduced pressure
  4. additionMethanol was then added to the residue
  5. filtrationthe resulting solution was filtered
  6. customto remove insoluble material
  7. customThe filtrate was evaporated to dryness under reduced pressure
  8. washthe residue was washed with ethanol

출처 및 근거

ORD 기록
ord-95c0d2d441694e68a2d01dbdeeb29b40
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04997943

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