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

HRID 1742950

Reaktionsgleichung

Reaktionsgleichung von HRID 1742950
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[N:23]1([CH:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)[CH:27]=[CH:26][N:25]=[N:24]1.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([CH3:17])[C:10]([F:16])=[C:11]([N:30]4[CH2:31][CH2:32][CH:28]([N:23]5[CH:27]=[CH:26][N:25]=[N:24]5)[CH2:29]4)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:2][CH2:3]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 190059431-(pyrrolidin-3-yl)-1H-1,2,3-triazole hydrochloride

Produkt 1

HCID 190060021-Cyclopropyl-6,8-difluoro-5-methyl-7-[3-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acidAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1-Cyclopropyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (30 mg, 0.1 mmol) was reacted with 35 mg (0.2 mmol) of 3-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride in 2 ml of dry pyridine under nitrogen in the presence of 30.4 mg (0.2 mmol) of DBU under reflux conditions. The solvent was removed under reduced pressure and to the orange viscous oil water was added and the solid was collected which was further purified from methanol to yield 20 mg of the desired product, m.p. 228°-230° C. 1H NMR (TFA) δ: 9.28 (s, 1H), 8.68 (s, 1H), 8.57 (d, 1.4Hz, 1H), 5.9-5.75 (m, 4.14 (m, 5H), 3.1-2.72 (m, 5H), 1.7-1.2 (m, 4H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure and to the orange viscous oil water
  2. additionwas added
  3. customthe solid was collected which
  4. customwas further purified from methanol

Quellen und Nachweise

ORD-Eintrag
ord-57603d4655a44489b744de693e5725f5
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05342846

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