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Triethylamine → 7-(3,3-Dimethoxy-4-methylpyrrolidin-1-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,8-naphthyridine-3-carboxylic acid

HRID 846702
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 846702
[CH3:1][O:2][C:3]1([O:9][CH3:10])[CH:7]([CH3:8])[CH2:6][NH:5][CH2:4]1.C([O:13][C:14]([C:16]1[CH2:17][N:18]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=2[F:35])[C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([F:26])=[C:21](Cl)[N:20]=2)=[O:15])C.C(N(CC)CC)C>N1C=CC=CC=1>[CH3:1][O:2][C:3]1([O:9][CH3:10])[CH:7]([CH3:8])[CH2:6][N:5]([C:21]2[N:20]=[C:19]3[C:24]([CH:25]=[C:16]([C:14]([OH:15])=[O:13])[CH2:17][N:18]3[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[F:35])=[CH:23][C:22]=2[F:26])[CH2:4]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 198833363,3-Dimethoxy-4-methylpyrrolidineHCID 867460661-(2,4-Difluorophenyl)-7-chloro-6-fluoro-1,8-naphthyridine-3-carboxylic acid ethyl ester

Produkt 1

HCID 198832787-(3,3-Dimethoxy-4-methylpyrrolidin-1-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,8-naphthyridine-3-carboxylic acidAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049
Pyridine
Lösungsmittel

Versuchsvorschrift

In a reaction similar to that of Step 1, Example 387, into oven-dried glassware maintained under dry N2 were placed 0.132 g (0.91 mmol) of 3,3-dimethoxy-4-methylpyrrolidine (from Step 5 Example 183), 0.300 g (0.78 mmol) of 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester, 12 mL of dry pyridine and 0.437 mL (3.1 mmol) of triethylamine. The reaction was stirred at room temperature for 15 hours, then the solvent was removed in a rotary evaporator. The residue was dissolved in methylene chloride and the product purified by column chromatography over silica gel, eluting with 0.5% increasing to 3% methanol/methylene chloride which was evaporated to afford 0.240 g of the title compound. This material was taken directly to the next step.

Aufarbeitung

  1. customIn a reaction similar to that of Step 1, Example 387
  2. custominto oven-dried glassware
  3. temperaturemaintained under dry N2
  4. customthe solvent was removed in a rotary evaporator
  5. dissolutionThe residue was dissolved in methylene chloride
  6. customthe product purified by column chromatography over silica gel
  7. washeluting with 0.5%
  8. temperatureincreasing to 3% methanol/methylene chloride which
  9. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-28e200da467b420dbfb0253a2b0b28c5
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05137892

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