Tetrahydrofuran → 1-(2,4-Difluorophenyl)-6-fluoro-7-[3-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 1742938

Reaktionsgleichung

Reaktionsgleichung von HRID 1742938
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:29])=[C:16]([N:19]3[CH2:23][CH2:22][CH:21]([N:24]4[CH:28]=[CH:27][N:26]=[N:25]4)[CH2:20]3)[N:17]=2)[C:12](=[O:30])[C:11]([C:31]([O:33]CC)=[O:32])=[CH:10]1.C1COCC1.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:29])=[C:16]([N:19]3[CH2:23][CH2:22][CH:21]([N:24]4[CH:28]=[CH:27][N:26]=[N:25]4)[CH2:20]3)[N:17]=2)[C:12](=[O:30])[C:11]([C:31]([OH:33])=[O:32])=[CH:10]1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 19006029Ethyl 1-(2,4-difluorophenyl)-6-fluoro-7-[3-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Produkt 1

HCID 190060251-(2,4-Difluorophenyl)-6-fluoro-7-[3-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of crude ethyl 1-(2,4-difluorophenyl) -6-fluoro-7-[3-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (150 mg, 0.31 mmol), THF (15 ml), NaOH (20 mg, 1.5 mmol) and water (15 ml) was heated under reflux for 3 h, cooled and the THF was evaporated. The residue was diluted with water, aqueous solution was acidified and the precipitated yellow solid was filtered, washed with water, dried in vac-oven at 50° C. This solid was washed with ether to get the pure compound. Yield: 50 mg (35.7%), m.p. 253° C. (dec). 1H NMR (TFA) δ: 2.85 (m, 2H), 3.70-4.50 (m, 4H), 5.80 (m, 1H), 7.20 (m, 2H), 7.60 (m, 1H), 8.25 (s, 1H), 8.57 (s, 1H), 8.62 (s, 1H), 9.20 (s, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperaturecooled
  4. customthe THF was evaporated
  5. additionThe residue was diluted with water, aqueous solution
  6. filtrationthe precipitated yellow solid was filtered
  7. washwashed with water
  8. customdried in vac-oven at 50° C
  9. washThis solid was washed with ether
  10. customto get the pure compound

Quellen und Nachweise

ORD-Eintrag
ord-6ccba68d7ded4f8189c31c91801e0b73
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05342846

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