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Triethylamine → 7-(2-Aminomethyl-1,4-dioxa-7-azaspiro[4.4]non-7-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,8-naphthyridine-3-carboxylic acid dihydrochloride

HRID 846701
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 846701
C(OC([NH:8][CH2:9][CH:10]1[CH2:14][O:13][C:12]2([CH2:18][CH2:17][NH:16][CH2:15]2)[O:11]1)=O)(C)(C)C.C([O:21][C:22]([C:24]1[CH2:25][N:26]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=2[F:43])[C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([F:34])=[C:29]([Cl:35])[N:28]=2)=[O:23])C.C(N(CC)CC)C>N1C=CC=CC=1>[ClH:35].[ClH:35].[NH2:8][CH2:9][CH:10]1[CH2:14][O:13][C:12]2([CH2:18][CH2:17][N:16]([C:29]3[N:28]=[C:27]4[C:32]([CH:33]=[C:24]([C:22]([OH:23])=[O:21])[CH2:25][N:26]4[C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=4[F:43])=[CH:31][C:30]=3[F:34])[CH2:15]2)[O:11]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 198832752-t-Butoxycarbonylaminomethyl-1,4-dioxa-7-azaspiro[4.4]nonaneHCID 867460661-(2,4-Difluorophenyl)-7-chloro-6-fluoro-1,8-naphthyridine-3-carboxylic acid ethyl ester

Produkt 1

HCID 678359397-(2-Aminomethyl-1,4-dioxa-7-azaspiro[4.4]non-7-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,8-naphthyridine-3-carboxylic acid dihydrochlorideAusbeute 232,8 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

In a reaction similar to that of Step 1 Example 387, into oven-dried glassware maintained under dry N2 were placed 0.733 g (2.8 mmol) of 2-t-butoxycarbonylaminomethyl-1,4-dioxa-7-azaspiro[4.4]nonane, from Step 5 Example 159, 0.725 g (1.9 mmol) of 1-(2,4-difluorophenyl)-7-chloro-6-fluoro-1,8-naphthyridine-3-carboxylic acid ethyl ester dissolved in 20 mL of pyridine and 1.06 mL (7.6 mmol) of triethylamine. The reaction was stirred at 45° C. for 6 hours, then the solvent was removed in a rotary evaporator after toluene was added to azeotrope the pyridine. The residue was dissolved in 60 mL of methylene chloride, washed with 2×50 mL of water and dried over anhydrous sodium sulfate and filtered. The solvent was removed by evaporation and the product was washed with hexane and dried to afford 1.184 g of the title compound, MS (DCl) M/Z 605 (M+H). NMR (CDCl3) d 1.40 (t, 3H, J=6 Hz), 1.47 (s, 9H), 2.03 (m, 2H), 3.16 (m, 2H), 3.51 (m, 4H), 3.69 (m, 1H), 4.04 (m, 1H), 4.22 (m, 1H), 4.38 (q, 2H, J=6 Hz), 4.81 (m, 1H), 7.05 (m, 2H), 7.38 (m, 1H), 8.09 (dd, 1H, J=12, 1.5 Hz), 8.39 (d, 1H, J=1.5 Hz).

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 after toluene
  5. additionwas added
  6. dissolutionThe residue was dissolved in 60 mL of methylene chloride
  7. washwashed with 2×50 mL of water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solvent was removed by evaporation
  11. washthe product was washed with hexane
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4faf6975aee54864a5f472150729c2a7
Quelldatensatz
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05137892

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