5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → HCID 19005970, Verbindung

HRID 1742965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742965
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.Cl.Cl.[NH2:24][C:25]1[N:26]=[N:27][N:28]([CH:30]2[CH2:34][CH2:33][NH:32][CH2:31]2)[CH:29]=1.N1(C2CCCCCCCCCC2)CCCCCCCCCN1>N1C=CC=CC=1>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:32]2[CH2:33][CH2:34][CH:30]([N:28]3[CH:29]=[C:25]([NH2:24])[N:26]=[N:27]3)[CH2:31]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Komponenten

5

Edukt 3

HCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 190059383-(4-Amino-1,2,3-triazol-1-yl)pyrrolidine dihydrochlorideHCID 57346892Diazabicycloundecane

Produkt 1

HCID 19005970HCID 19005970, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (100 mg, 0.67 mmol), 3-(4-amino-1,2,3-triazol-1-yl)pyrrolidine dihydrochloride (185 mg, 0.83 mmol) and diazabicycloundecane (127 mg, 0.83 mmol) in pyridine (3 ml) was heated at 110° C. for 24 hrs. Reaction mixture was concentrated to dryness under vacuum and residue was dissolved in water, extracted with methylene chloride, dried over sodium sulfate and concentrated to dryness. The solid residue thus obtained was crystallized from chloroform to brown solid. Yield 15 mg (10.4%), m.p. 210°-213° C. 1H NMR (TFA) δ: 1.22-1.58 (m, 4H), 2.70-2.90 (m, 2H), 4.06-4.54 (m, 5H), 5.48-5.60 (m, 1H), 7.79 (s, 1H), 9.14 (s, 1H).

Aufarbeitung

  1. customReaction mixture
  2. concentrationwas concentrated to dryness under vacuum and residue
  3. dissolutionwas dissolved in water
  4. extractionextracted with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe solid residue thus obtained
  8. customwas crystallized from chloroform to brown solid

Quellen und Nachweise

ORD-Eintrag
ord-070d1e6bd67f481c8ebd872ac55b8ecd
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05342846

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