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 1742978

Reaktionsgleichung

[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

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

concentrationconcentrated to dryness
additionThe residue was diluted with water and thus solid
customseparated
filtrationwas filtered
washwashed thoroughly with water
customdried

Quellen und Nachweise

ORD-Eintrag: ord-67334727eab342d3887688f374fa0a84
Quelldatensatz: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05342846

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