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

HRID 1742979Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742979
[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][CH2:17][CH:16]([N:20]5[CH:24]=[CH:23][N:22]=[N:21]5)[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[CH2:19][CH2:18][CH2:17][CH:16]([N:20]5[CH:24]=[CH:23][N:22]=[N:21]5)[CH2:15]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 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

Produkt 1

HCID 190059821-Cyclopropyl-6-fluoro-7-[3-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acidAusbeute 35,9 %

Versuchsvorschrift

A mixture of 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 (90 mg, 0.21 mmol) and 6N-HCl (5 ml) was heated to 100°-110° C. for 6 hrs. The mixture was concentrated and the residue was diluted with water. The pH of aqueous solution was adjusted to 7 by the addition of NH4OH and thus separated solid was filtered, washed with water, acetonitrile and dried to give 30 mg of desired product. m.p. 251°-254° C.; 1H NMR (TFA) δ: 9.25 (s, 1H), 8.65 (s, 1H), 8.55 (s, 1H), 8.22 (d, 1H), 5.37 (m, 1H), 5.15 (m, 1H), 4.38-4.75 (m, 2H), 4.10 (m, 2H), 2.45-2.85 (m, 2H), 2.00-2.40 (m, 2H), 1.22-1.65 (m, 4H).

Aufarbeitung

  1. temperaturewas heated to 100°-110° C. for 6 hrs
  2. concentrationThe mixture was concentrated
  3. additionthe residue was diluted with water
  4. additionThe pH of aqueous solution was adjusted to 7 by the addition of NH4OH and thus separated solid
  5. filtrationwas filtered
  6. washwashed with water, acetonitrile
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7821debf2de340388ea987283b941acc
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05342846

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