1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-Cyclopropyl-6,8-difluoro-5-methyl-7-[3-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1742974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1742974
Cl.[N:2]1([CH:7]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][N:4]=[N:3]1.C1CCN2C(=NCCC2)CC1.[CH3:24][C:25]1[C:34]([F:35])=[C:33](F)[C:32]([F:37])=[C:31]2[C:26]=1[C:27](=[O:44])[C:28]([C:41]([OH:43])=[O:42])=[CH:29][N:30]2[CH:38]1[CH2:40][CH2:39]1>C(#N)C>[CH:38]1([N:30]2[C:31]3[C:26](=[C:25]([CH3:24])[C:34]([F:35])=[C:33]([N:9]4[CH2:10][CH2:11][CH2:12][CH:7]([N:2]5[CH:6]=[CH:5][N:4]=[N:3]5)[CH2:8]4)[C:32]=3[F:37])[C:27](=[O:44])[C:28]([C:41]([OH:43])=[O:42])=[CH:29]2)[CH2:39][CH2:40]1

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 146512581-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 190059273-(1H-1,2,3-triazol-1-yl)piperidine hydrochloride

Produkt 1

HCID 190060361-Cyclopropyl-6,8-difluoro-5-methyl-7-[3-(1,2,3-triazol-1-yl)piperidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acidAusbeute 47,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-(1,2,3-triazol-1-yl)piperidine hydrochloride (63 mg, 0.33 mmol) and DBU (77 mg, 0.5 mmol) were added to a suspension of 5-methyl-1-cyclopropyl-6,7,8-trifluoro -1,4-dihydro-4-oxoquinoline-3-carboxylic acid (50 mg, 0.17 mmol) in acetonitrile (5 ml). The reaction mixture was refluxed under stirring for 66 hrs and then concentrated. The residue was diluted with water and thus separated solid was filtered, washed with water, acetonitrile and dried to give 35 mg of desired product. m.p. 227°-228.5° C.; 1H NMR (TFA) δ: 9.35 (s, 1H), 8.53 (s, 1H), 8.65 (s, 1H), 5.30 (m, 1H), 4.60 (m, 1H), 3.55-4.35 (m, 4H), 2.90 (s, 3H), 2.08-2.75 (m, 4H), 1.30-1.55 (m, 4H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed
  2. concentrationconcentrated
  3. additionThe residue was diluted with water and thus separated solid
  4. filtrationwas filtered
  5. washwashed with water, acetonitrile
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-38fb41a1c5dd49dea70f384f7b615bc3
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05342846

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