Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate → Ethyl 1-cyclopropyl-6-fluoro-7-[3-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 1742978Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742978
[N:1]1([CH:6]2[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]2)[CH:5]=[CH:4][N:3]=[N:2]1.[CH:12]1([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:26])=[C:22](Cl)[N:23]=3)[C:18](=[O:27])[C:17]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:16]2)[CH2:14][CH2:13]1>C(#N)C.N1C=CC=CC=1>[CH:12]1([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:26])=[C:22]([N:8]4[CH2:9][CH2:10][CH2:11][CH:6]([N:1]5[CH:5]=[CH:4][N:3]=[N:2]5)[CH2:7]4)[N:23]=3)[C:18](=[O:27])[C:17]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:16]2)[CH2:13][CH2:14]1

Komponenten

5

Edukt 2

HCID 11722954Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateHCID 190059283-(1H-1,2,3-Triazol-1-yl)piperidine

Produkt 1

HCID 19005955Ethyl 1-cyclopropyl-6-fluoro-7-[3-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3-(1,2,3-triazol-1-yl)piperidine (150 mg, 0.96 mmol) was added to a solution of ethyl 1-cyclopropyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (150 mg, 0.48 mmol) in a mixture of acetonitrile (10 ml) and pyridine (3 ml). The reaction mixture was heated at 100° C. for 6 hrs and then concentrated to dryness. The residue was diluted with water and thus solid separated was filtered, washed thoroughly with water and dried. Yield 90 mg, m.p. 205°-206° C.; 1H NMR (CDCl3) δ: 8.58 (s, 1H), 8.15 (d, 1H), 7.78 (s, 1H), 7.65 (s, 1H), 4.90 (m, 2H), 4.40 (m, 3H), 3.45 (m, 3H), 1.75-2.50 (m, 4H), 1.40 (t, 3H), 0.95-1.35 (m, 4H).

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. additionThe residue was diluted with water and thus solid
  3. customseparated
  4. filtrationwas filtered
  5. washwashed thoroughly with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-67334727eab342d3887688f374fa0a84
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05342846

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