Hydrochloric Acid → 1-Cyclopropyl-6-fluoro-7-[4-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

HRID 1742981

Reaktionsgleichung

Reaktionsgleichung von HRID 1742981
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:14]4[CH2:19][CH2:18][CH:17]([N:20]5[CH:24]=[CH:23][N:22]=[N:21]5)[CH2:16][CH2:15]4)[N:12]=3)[C:7](=[O:26])[C:6]([C:27]([O:29]CC)=[O:28])=[CH:5]2)[CH2:3][CH2:2]1.Cl>>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:25])=[C:11]([N:14]4[CH2:15][CH2:16][CH:17]([N:20]5[CH:24]=[CH:23][N:22]=[N:21]5)[CH2:18][CH2:19]4)[N:12]=3)[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:2][CH2:3]1

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 19005933Ethyl 1-cyclopropyl-6-fluoro-7-[4-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Produkt 1

HCID 190059831-Cyclopropyl-6-fluoro-7-[4-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acidAusbeute 47,1 %

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of ethyl 1-cyclopropyl-6-fluoro-7-[4-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (135 mg, 0.32 mmol) and 6N-HCl (6 ml) was heated at 110° C. for 18 hrs. The reaction mixture was concentrated and the residue was diluted with water. The pH of the suspension was adjusted to 7 by addition of NH4OH and this separated solid was filtered, washed with water, CH3CN and dried to give 60 mg of title product. m.p. 246°-248° C.; 1H NMR (TFA) δ: 9.25 (s, 1H), 8.65 (s, 1H), 8.52 (s, 1H), 8.25 (d, 1H), 5.35 (m, 3H), 4.12 (m, 1H), 3.75 (m, 2H), 2.40-2.85 (m, 4H), 1.25-1.70 (m, 4H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with water
  3. additionThe pH of the suspension was adjusted to 7 by addition of NH4OH
  4. filtrationthis separated solid was filtered
  5. washwashed with water, CH3CN
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9988888e9304472f9144851b2245d19f
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05342846

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